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Technology Process of 2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid

2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid

Base Information Edit
  • Chemical Name:2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid
  • CAS No.:55898-33-4
  • Molecular Formula:C34H60O10
  • Molecular Weight:628.844
  • Hs Code.:
  • Wikidata:Q77494445
  • Metabolomics Workbench ID:109104
  • Mol file:55898-33-4.mol
2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid

Synonyms:

Suppliers and Price of 2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • American Custom Chemicals Corporation
  • LYSOCELLIN 95.00%
  • 5MG
  • $ 498.69
Total 3 raw suppliers
Chemical Property of 2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid Edit
Chemical Property:
  • Vapor Pressure:3.98E-24mmHg at 25°C 
  • Refractive Index:1.5376 (estimate) 
  • Boiling Point:722.8°Cat760mmHg 
  • PKA:4.38±0.10(Predicted) 
  • Flash Point:216°C 
  • PSA：151.98000 
  • Density:1.104g/cm3 
  • LogP:4.89920 
  • XLogP3:4.7
  • Hydrogen Bond Donor Count:5
  • Hydrogen Bond Acceptor Count:10
  • Rotatable Bond Count:13
  • Exact Mass:628.41864811
  • Heavy Atom Count:44
  • Complexity:1020
Purity/Quality:

99% *data from raw suppliers

LYSOCELLIN 95.00% *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CCC(C1C(CC(O1)(C)C2(C(CC(O2)(CC)C(CC)O)C)O)C)C(=O)C(C)C(C(C)C3C(CC(C(O3)(CC(=O)O)O)C)C)O
  • Isomeric SMILES:CC[C@H]([C@@H]1[C@H](C[C@@](O1)(C)[C@]2([C@@H](C[C@](O2)(CC)[C@H](CC)O)C)O)C)C(=O)[C@@H](C)[C@H]([C@H](C)[C@@H]3[C@H](C[C@H]([C@@](O3)(CC(=O)O)O)C)C)O
Technology Process of 2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid

There total 84 articles about 2-[(2S,3R,5S,6S)-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2-hydroxy-3,5-dimethyloxan-2-yl]acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane
144534-92-9

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

Lysocellin
55898-33-4

Lysocellin

Guidance literature:
Multi-step reaction with 19 steps
1: 1.) t-BuLi / 1.) ether, -78 deg C
2: Swern oxidation
3: diethyl ether / -78 to -20 deg C
4: DDQ / CH2Cl2; H2O / Ambient temperature
5: LiAlH4 / diethyl ether / 0 °C
6: pyridine / 0 °C
7: 1N H2SO4 / tetrahydrofuran / Ambient temperature
8: K2CO3 / methanol / Ambient temperature
9: CSA / CH2Cl2 / 0 °C
10: imidazole / CH2Cl2 / 0 deg C to room temp.
11: TEA, DMAP / CH2Cl2 / Ambient temperature
12: 1N HCl / tetrahydrofuran / Ambient temperature
13: Swern oxidation
14: tetrahydrofuran / -78 to -20 deg C
15: n-Bu4NF / dimethylformamide / Ambient temperature
16: 69 percent / PCC, 3A-molecular sieves / CH2Cl2 / Ambient temperature
17: 70 percent / 1N H2SO4 / tetrahydrofuran / 0 deg C to room temp.
18: 77 percent / H2 / Raney Ni (W-2) / ethanol / Ambient temperature
19: 1.) LDA, ZnCl2 / 1.) THF, -78 deg C
With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 3 A molecular sieve; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium carbonate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; lithium diisopropyl amide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane
144534-92-9

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

((2S,3R,5S,6S)-6-{(1S,2R,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid
55898-33-4,108691-72-1

((2S,3R,5S,6S)-6-{(1S,2R,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:
Multi-step reaction with 19 steps
1: 1.) t-BuLi / 1.) ether, -78 deg C
2: Swern oxidation
3: diethyl ether / -78 to -20 deg C
4: DDQ / CH2Cl2; H2O / Ambient temperature
5: LiAlH4 / diethyl ether / 0 °C
6: pyridine / 0 °C
7: 1N H2SO4 / tetrahydrofuran / Ambient temperature
8: K2CO3 / methanol / Ambient temperature
9: CSA / CH2Cl2 / 0 °C
10: imidazole / CH2Cl2 / 0 deg C to room temp.
11: TEA, DMAP / CH2Cl2 / Ambient temperature
12: 1N HCl / tetrahydrofuran / Ambient temperature
13: Swern oxidation
14: tetrahydrofuran / -78 to -20 deg C
15: n-Bu4NF / dimethylformamide / Ambient temperature
16: 69 percent / PCC, 3A-molecular sieves / CH2Cl2 / Ambient temperature
17: 70 percent / 1N H2SO4 / tetrahydrofuran / 0 deg C to room temp.
18: 77 percent / H2 / Raney Ni (W-2) / ethanol / Ambient temperature
19: 1.) LDA, ZnCl2 / 1.) THF, -78 deg C
With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 3 A molecular sieve; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium carbonate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; lithium diisopropyl amide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane
144534-92-9

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

((2S,3R,5S,6S)-6-{(1S,2S,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid
55898-33-4,108691-72-1

((2S,3R,5S,6S)-6-{(1S,2S,3R,5R)-5-[(2S,4S,5S,2'R,3'R,5'R)-5'-Ethyl-2'-hydroxy-5'-((S)-1-hydroxy-propyl)-2,4,3'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-2-hydroxy-1,3-dimethyl-4-oxo-heptyl}-2-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:
Multi-step reaction with 19 steps
1: 1.) t-BuLi / 1.) ether, -78 deg C
2: Swern oxidation
3: diethyl ether / -78 to -20 deg C
4: DDQ / CH2Cl2; H2O / Ambient temperature
5: LiAlH4 / diethyl ether / 0 °C
6: pyridine / 0 °C
7: 1N H2SO4 / tetrahydrofuran / Ambient temperature
8: K2CO3 / methanol / Ambient temperature
9: CSA / CH2Cl2 / 0 °C
10: imidazole / CH2Cl2 / 0 deg C to room temp.
11: TEA, DMAP / CH2Cl2 / Ambient temperature
12: 1N HCl / tetrahydrofuran / Ambient temperature
13: Swern oxidation
14: tetrahydrofuran / -78 to -20 deg C
15: n-Bu4NF / dimethylformamide / Ambient temperature
16: 69 percent / PCC, 3A-molecular sieves / CH2Cl2 / Ambient temperature
17: 70 percent / 1N H2SO4 / tetrahydrofuran / 0 deg C to room temp.
18: 77 percent / H2 / Raney Ni (W-2) / ethanol / Ambient temperature
19: 1.) LDA, ZnCl2 / 1.) THF, -78 deg C
With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 3 A molecular sieve; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium carbonate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; lithium diisopropyl amide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1
upstream raw materials:

<2S-<2α<2'R*,3'S*,5'S(R*)>4α,5β(S*)>>-4-<5'-ethyl-5'-(1-hydroxypropyl)octahydro-2'-hydroxy-2,3',4-trimethyl<2,2'-bifuran>-5-yl>-3-hexanone

2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetic acid

(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol

Refernces Edit

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