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

Base Information

Chemical Name:Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:289057-13-2
Molecular Formula:C₂₈H₃₈BrClO₆Si
Molecular Weight:614.049
Hs Code.:

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

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

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

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

: 289057-11-0
ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

: 289057-13-2
Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With 4 A molecular sieve; bromine; In dichloromethane; for 0.166667h;
DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

: 100-39-0
benzyl bromide

: 289057-13-2
Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 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

4: Br₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; bromine; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Acylation / 4: Bromination;
DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

: 153185-20-7
ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

: 289057-13-2
Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 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

4: Br₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; bromine; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Acylation / 4: Bromination;
DOI:10.1016/S0040-4020(00)00239-8