ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS No.: 127840-80-6
• Molecular Formula: C₆₃H₆₂O₁₃S
• Molecular Weight: 1059.24
• Mol file: 127840-80-6.mol

Synonyms:ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 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: 91.0%

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) + ethyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside (35784-52-2) → ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (127840-80-6)

Guidance literature:

With molecular sieve; iodonium di(2,4,6-trimethylpyridine) perchlorate; In diethyl ether; 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)94391-0

Reference yield: 61.0%

ethyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside (35784-52-2) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran (197164-69-5) → ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (127840-80-6)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 Angstroem MS; In diethyl ether; dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1021/jo971233k

Reference yield:

benzyl bromide (100-39-0) → ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (127840-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / NaH / dimethylformamide / 18 h / Ambient temperature

2: 61 percent / 4 Angstroem MS, NIS, TfOH / CH₂Cl₂; diethyl ether / 0.08 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 Angstroem MS; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971233k

upstream raw materials:

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

ethyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside

(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran

benzyl bromide

Downstream raw materials:

1-thioethylhepta-o-benzoyl-β-D-maltose