(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

Base Information

Chemical Name:(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside
CAS No.:334536-27-5
Molecular Formula:C₂₇H₃₅BrO₇
Molecular Weight:551.475
Hs Code.:

Synonyms:(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

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Chemical Property of (2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

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Technology Process of (2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

There total 6 articles about (2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside 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: 92.0%

: 334536-13-9
(2-hydroxy-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

: 334536-27-5
(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

Guidance literature:: With N-Bromosuccinimide; triphenylphosphine; In N,N-dimethyl-formamide; at 70 ℃; for 0.5h;
DOI:10.1016/S0968-0896(00)00256-X

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 334536-27-5
(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NaH / dimethylformamide / 16 h

2: 98 percent / O₃; NaBH₄ / methanol; tetrahydrofuran

3: 92 percent / N-bromosuccinimide; Ph₃P / dimethylformamide / 0.5 h / 70 °C

With sodium tetrahydroborate; N-Bromosuccinimide; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: etherification / 2: ozonolysis; reduction / 3: bromination;
DOI:10.1016/S0968-0896(00)00256-X

Reference yield:

: 100-39-0
benzyl bromide

: 334536-27-5
(2-bromo-ethyl) 2,3-di-O-benzyl-4-O-(tert-butoxycarbonylmethyl)-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 16 h / 20 °C

2: 97 percent / NaH / dimethylformamide / 16 h

3: 98 percent / O₃; NaBH₄ / methanol; tetrahydrofuran

4: 92 percent / N-bromosuccinimide; Ph₃P / dimethylformamide / 0.5 h / 70 °C

With sodium tetrahydroborate; N-Bromosuccinimide; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: etherification / 2: etherification / 3: ozonolysis; reduction / 4: bromination;
DOI:10.1016/S0968-0896(00)00256-X