(2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone

Base Information

• Chemical Name: (2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone
• CAS No.: 115250-38-9
• Molecular Formula: C35H36O6
• Molecular Weight: 552.667
• DSSTox Substance ID: DTXSID90452397
• Nikkaji Number: J1.361.185H
• Wikidata: Q72482115
• Mol file: 115250-38-9.mol

Synonyms:115250-38-9;(2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone;(2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone;(2R,3S,4S,5S)-5-hydroxy-2,3,4-tris(phenylmethoxy)-5-(phenylmethoxymethyl)cyclohexan-1-one;(2R,3S,4S,5S) -5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone;SCHEMBL49399;DTXSID90452397;(2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)-methyl)-5-hydroxycyclohexanone;(2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexan-1-one;MFCD09838991;AKOS016011227;F15961;A893908;2alpha,3beta,4alpha-Tris(benzyloxy)-5alpha-hydroxy-5-(benzyloxymethyl)cyclohexanone;(3S,4S,5S,2R)-5-hydroxy-5-[(phenylmethoxy)methyl]-2,3,4-tris(phenyl methoxy)cyclohexan-1-one

Chemical Property of (2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 84-85 °C
• Refractive Index: 1.624
• Boiling Point: 681.917 °C at 760 mmHg
• PKA: 12.23±0.70(Predicted)
• Flash Point: 214.079 °C
• PSA: 74.22000
• Density: 1.232 g/cm³
• LogP: 5.66330
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 552.25118886
• Heavy Atom Count: 41
• Complexity: 750

Purity/Quality:

99% ^*data from raw suppliers

(2R,?3S,?4S,?5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)C(C(C(C1(COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1C(=O)[C@@H]([C@H]([C@@H]([C@]1(COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: (2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone was used in the synthetic preparation of N-substituted valiolamine derivatives. (2R,?3S,?4S,?5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone was used in the synthetic preparation of N-substituted valiolamine derivatives.

Technology Process of (2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone

There total 25 articles about (2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexanone 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%

1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-L-xylo-hept-6-en-2-ulose (261713-62-6) → (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol (115250-38-9)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; water; for 4h; Heating;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield: 88.5%

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol (116308-18-0) → (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol (115250-38-9)

Guidance literature:

With water; ammonium chloride; zinc; In acetonitrile; at 30 - 35 ℃; Reagent/catalyst; Temperature;

Reference yield: 83.0%

1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(2,2-dimethyl-3-oxopropyl)-L-xylo-hept-6-en-2-ulose (261713-64-8) → (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol (115250-38-9)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; water; for 4h; Heating;

DOI:10.1016/S0040-4020(00)00621-9

upstream raw materials:

(1S)-(1(OH),2,4,6/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6-chloro-5-oxo-1,2,3,4-cyclohexanetetrol

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-6,6-bis(methylthio)-1,2,3,4-cyclohexanetetrol

1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(2,2-dimethyl-3-oxopropyl)-L-xylo-hept-6-en-2-ulose

Downstream raw materials:

(1S)-(1(OH),2,4,5/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-<<(1R,2R)-2-hydroxycyclohexyl>amino>-1,2,3,4-cyclohexanetetrol

Refernces

• 1、 -. "Preparation method of voglibose intermediate". Paragraph 0026; 0027. . Retrieved 2016/11/17.
• 2、 -. "PROCESS FOR THE PREPARATION OF 1,2,3,4-CYCLOHEXANETETROL DERIVATIVES". Page/Page column 15. . Retrieved 2008/06/13.