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

Base Information

• Chemical Name: dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS No.: 250122-23-7
• Molecular Formula: C₆₀H₇₀O₁₂S
• Molecular Weight: 1015.27
• Mol file: 250122-23-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-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: 89.0%

dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside → dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-1-thio-β-D-glucopyranoside (250122-23-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jo990836o

Reference yield:

dicyclohexylmethyl 1-thio-β-D-glucopyranoside (197164-66-2) → dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-1-thio-β-D-glucopyranoside (250122-23-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / CSA / dimethylformamide / 18 h / 20 °C

2: 40 percent / NIS; TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -70 °C

3: 98 percent / DMAP / pyridine / 18 h / 20 °C

4: 89 percent / aq. TFA / acetonitrile; CH₂Cl₂ / 3 h / 20 °C

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; trifluoroacetic acid; In pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Cycloaddition / 2: Condensation / 3: Acylation / 4: Ring cleavage;

DOI:10.1021/jo990836o

Reference yield:

dicyclohexylmethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside → dicyclohexylmethyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-O-benzoyl-1-thio-β-D-glucopyranoside (250122-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / NIS; TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -70 °C

2: 98 percent / DMAP / pyridine / 18 h / 20 °C

3: 89 percent / aq. TFA / acetonitrile; CH₂Cl₂ / 3 h / 20 °C

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In pyridine; diethyl ether; dichloromethane; acetonitrile; 1: Condensation / 2: Acylation / 3: Ring cleavage;

DOI:10.1021/jo990836o

upstream raw materials:

dicyclohexylmethyl 1-thio-β-D-glucopyranoside

Downstream raw materials:

dicyclohexylmethyl 6-O-(6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-3-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)]-2-O-benzoyl-1-thio-β-D-glucopyranoside