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

Base Information

• Chemical Name: dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS No.: 171503-76-7
• Molecular Formula: C₇₄H₈₆O₁₀S
• Molecular Weight: 1167.56
• Mol file: 171503-76-7.mol

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

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

There total 10 articles about dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-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: 71.0%

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) + ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-yl)-methanol (197164-82-2) → dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (171503-76-7)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In diethyl ether; dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/0040-4039(95)01222-4

Reference yield: 50.0%

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-yl)-methanol (197164-82-2) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran (197164-69-5) → dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (171503-76-7)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In diethyl ether; dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo971233k

Reference yield:

benzyl bromide (100-39-0) → dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (171503-76-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide / 18 h / Ambient temperature

2: acetic acid; H₂O / 18 h / 60 °C

3: 71 percent / 4 Angstroem MS, iodonium dicollidine perchlorate / CH₂Cl₂; diethyl ether / 2 h / Ambient temperature

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 Angstroem MS; sodium hydride; In diethyl ether; dichloromethane; water; acetic acid; 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

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

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

benzyl bromide