ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside
• CAS No.: 289057-11-0
• Molecular Formula: C₃₀H₄₃ClO₆SSi
• Molecular Weight: 595.272
• Mol file: 289057-11-0.mol

Synonyms:ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

There total 4 articles about ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside 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: 100.0%

chloroacetyl chloride (79-04-9) + ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (289057-10-9) → ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside (289057-11-0)

Guidance literature:

With pyridine; In dichloromethane; for 0.0833333h;

DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

benzyl bromide (100-39-0) → ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside (289057-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH / dimethylformamide / 0.25 h

2: 85 percent / BH₃*Me₃N; AlCl₃; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.17 h

3: 100 percent / pyridine / CH₂Cl₂ / 0.08 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Acylation;

DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (153185-20-7) → ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside (289057-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH / dimethylformamide / 0.25 h

2: 85 percent / BH₃*Me₃N; AlCl₃; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.17 h

3: 100 percent / pyridine / CH₂Cl₂ / 0.08 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Acylation;

DOI:10.1016/S0040-4020(00)00239-8

upstream raw materials:

chloroacetyl chloride

ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

benzyl bromide

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside