phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside
CAS No.:1441883-29-9
Molecular Formula:C₂₇H₃₅BrO₆SSi
Molecular Weight:595.627
Hs Code.:

Synonyms:phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

There total 5 articles about phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-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: 83.0%

: 922183-00-4
phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

: 598-21-0
2-Bromoacetyl bromide

: 1441883-29-9
phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/chem.201203725

Reference yield:

: 530-26-7
D-Mannose

: 1441883-29-9
phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic anhydride; iodine / 20 °C

1.2: 0 - 20 °C

1.3: 20 °C

2.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 50 °C / 76.01 Torr

3.1: di(n-butyl)tin oxide / toluene / 2 h / 110 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With pyridine; camphor-10-sulfonic acid; iodine; acetic anhydride; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203725

Reference yield:

: 108-98-5
thiophenol

: 1441883-29-9
phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic anhydride; iodine / 20 °C

1.2: 0 - 20 °C

1.3: 20 °C

2.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 50 °C / 76.01 Torr

3.1: di(n-butyl)tin oxide / toluene / 2 h / 110 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With pyridine; camphor-10-sulfonic acid; iodine; acetic anhydride; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203725