dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS No.: 197164-75-3
• Molecular Formula: C₄₇H₅₀O₉S
• Molecular Weight: 790.975
• Mol file: 197164-75-3.mol

Synonyms:dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property of dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

There total 4 articles about dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-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:

benzoyl chloride (98-88-4) + dicyclohexylmethyl 1-thio-β-D-glucopyranoside (197164-66-2) → dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (197164-75-3)

Guidance literature:

In pyridine;

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

Reference yield:

Dicyclohexyl-methanethiol → dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (197164-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / TMSOTf / CH₂Cl₂ / 16 h / Ambient temperature

2: NaOMe / CH₂Cl₂; methanol / 3 h

3: DMAP / pyridine / 18 h / Ambient temperature

With dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1021/jo971233k

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-67-6) → dicyclohexylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (197164-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / CH₂Cl₂; methanol / 3 h

2: DMAP / pyridine / 18 h / Ambient temperature

With dmap; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1021/jo971233k

upstream raw materials:

benzoyl chloride

dicyclohexylmethyl 1-thio-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

β-D-glucose pentaacetate

Downstream raw materials:

methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside