methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

Base Information

Chemical Name:methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside
CAS No.:1439381-80-2
Molecular Formula:C₂₇H₄₃BrO₇Si
Molecular Weight:587.624
Hs Code.:

Synonyms:methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

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Chemical Property of methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

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Technology Process of methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

There total 6 articles about methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside 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: 87.0%

: 1439381-79-9
4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

: 1439381-80-2
methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; at 0 ℃; for 2h; Reflux;
DOI:10.1021/ml400098w

Reference yield:

: methyl 4,6-O-benzylidene-3-deoxy-3-C-ethenyl-α-D-altropyranoside

: 1439381-80-2
methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3: sodium hydroxide; dihydrogen peroxide / 16 h / 20 °C / Inert atmosphere

4: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; dihydrogen peroxide; barium carbonate; sodium hydroxide; In tetrahydrofuran; tetrachloromethane; dichloromethane;
DOI:10.1021/ml400098w

Reference yield:

: methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(2-hydroxyethyl)-α-D-altropyranoside

: 1439381-80-2
methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

With pyridine; N-Bromosuccinimide; barium carbonate; In tetrachloromethane; dichloromethane;
DOI:10.1021/ml400098w