(3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one

Base Information

• Chemical Name: (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one
• CAS No.: 230636-19-8
• Molecular Formula: C₃₈H₄₄O₅S₂
• Molecular Weight: 644.896
• Mol file: 230636-19-8.mol

Synonyms:(3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one

Chemical Property of (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one

There total 3 articles about (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one 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: 81.0%

(2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol (53929-48-9) → (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one (230636-19-8)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 0.75h;

Reference yield: 54.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + ethanethiol (75-08-1) → (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one (230636-19-8)

Guidance literature:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose; ethanethiol; With trifluoroacetic acid; Inert atmosphere;

With acetic anhydride; In dimethyl sulfoxide; Inert atmosphere;

DOI:10.1039/c0ob00475h

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose → (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one (230636-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylbromosulphonium bromide / 2 h / 20 °C

2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.75 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With tetrapropylammonium perruthennate; dimethylbromosulphonium bromide; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.3390/molecules18056021

upstream raw materials:

(2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

ethanethiol

Downstream raw materials:

C₃₉H₄₆O₄S₂

dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-en-1-yl phosphate

dibenzyl (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-en-1-yl phosphate

dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate