CID 10982781

Base Information

• Chemical Name: CID 10982781
• CAS No.: 77674-99-8
• Molecular Formula: C20H28 N2 O8
• Molecular Weight: 424.451
• Mol file: 77674-99-8.mol

Synonyms:SCHEMBL3074791

Chemical Property of CID 10982781

Chemical Property:

• Vapor Pressure: 3.2E-29mmHg at 25°C
• Boiling Point: 830.3°C at 760 mmHg
• Flash Point: 456°C
• PSA: 182.90000
• Density: 1.381g/cm³
• LogP: 1.06900
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 424.18456586
• Heavy Atom Count: 30
• Complexity: 622

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C1CC2=C(C(=CC=C2)O)C(=O)O1)NC(=O)C(C(C(CC(=O)[O-])[NH3+])O)O
• Isomeric SMILES: CC(C)C[C@@H]([C@@H]1CC2=C(C(=CC=C2)O)C(=O)O1)NC(=O)[C@H]([C@H]([C@H](CC(=O)[O-])[NH3+])O)O

Technology Process of CID 10982781

There total 68 articles about CID 10982781 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: 90.0%

amicoumacin C hydrochloride (86594-32-3) → 6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate (77674-99-8)

Guidance literature:

amicoumacin C hydrochloride; With sodium hydroxide; water; In ethanol; for 16h; pH=9;

With hydrogenchloride; water; In ethanol; pH=6.5;

DOI:10.1002/anie.200804571

Reference yield: 75.0%

(4S,5S)-4-Benzyloxycarbonylmethyl-5-{(S)-benzyloxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (365449-64-5) → 6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate (77674-99-8)

Guidance literature:

With Dowex 50-X₈; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; at 23 ℃; for 12h;

DOI:10.1021/ol0101279

Reference yield:

ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → 6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate (77674-99-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature

2: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating

3: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min

4: 1) ozone, 2) pyridine / 1) CH₂Cl₂, -74 deg C, 2 h, 2) -74 deg C up to room temp.

5: 65 percent / OsO₄, N-methylmorpholine N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 15 h / Ambient temperature

6: 98 percent / PPTS / acetone / 10 h / Ambient temperature

7: 95 percent / methanol / 0.5 h / Heating

8: 95 percent / 18-crown-6, tri-n-butyl phosphine, CCl₄ / acetonitrile / 1a) 30-40 deg C, 1 h, 1b) 70-80 deg C, 2 h

9: 92 percent / DMAP / acetonitrile / 1 h / Ambient temperature

10: 70 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

11: 70 percent / DEPC, Et₃N / dimethylformamide / 1a) 0 deg C, 3 h, 1b) room temp., 20 h

With pyridine; tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; tributylphosphine; 4 A molecular sieve; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; diethyl dicarbonate; dmap; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)82406-6

upstream raw materials:

(S)-2-[(2S,3S)-3-amino-5-oxotetrahydrofuran-2-yl]-2-hydroxy-N-{(S)-1-[(S)-8-hydroxy-1-oxoisochroman-3-yl]-3-methylbutyl}acetamide

amicoumacin C hydrochloride

AI-77-G

((S)-2-Cyano-1-{(4S,5S)-5-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-carbamic acid tert-butyl ester

Downstream raw materials:

AI-77-G

6-<<1-(2-carboxy-3-hydroxyphenyl)-2-hydroxy-5-methylhex-3-yl>amino>-4,5-dihydroxy-6-oxo-3-ammoniohexanoate

L-leucine

<6-<<1-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl>amino>-4,5-dihydroxy-6-oxo-3-hexanamido>ammonium chloride

Refernces

• 1、 Wang, Hui-Hong,Li, Zhao,Feng, Yi-Yue,Yin, Gao-Feng,Shi, Tao,He, Dian,Wang, Xiao-Dong,Wang, Zhen. "Application of Pd-Catalyzed C-H Alkylation Reaction in Total Syntheses of Twelve Amicoumacin-Type Natural Products". supporting information. p. 6956 - 6960. Retrieved 2021/09/11.
• 2、 Enomoto, Masaru,Kuwahara, Shigefumi. "Total synthesis of bacilosarcins A and B". supporting information; experimental part. p. 1144 - 1148. Retrieved 2009/06/19.