Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

Base Information

Chemical Name:Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester
CAS No.:159327-92-1
Molecular Formula:C₃₁H₃₉BrO₇
Molecular Weight:603.55
Hs Code.:

Synonyms:Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

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Chemical Property of Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

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Technology Process of Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

There total 5 articles about Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl 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: 82.0%

: 22118-09-8
2-bromoacetyl chloride

: 159327-91-0
1-[(2S,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-ethanone

: 159327-92-1
Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 5h;
DOI:10.1021/ja00099a081

Reference yield:

: 131311-18-7
(2S,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

: 159327-92-1
Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / tetrahydrofuran / 1 h / 0 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CHCl₂, -78 deg C, 2.) CH₂Cl₂, 1 h

3: 100 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

4: 82 percent / pyridine / CH₂Cl₂ / 5 h / 0 °C

With pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00099a081

Reference yield:

: 131311-17-6
[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

: 159327-92-1
Bromo-acetic acid (2S,3S,4aR,6S,7R,8aS)-2-acetyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CHCl₂, -78 deg C, 2.) CH₂Cl₂, 1 h

2: 96 percent / tetrahydrofuran / 1 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CHCl₂, -78 deg C, 2.) CH₂Cl₂, 1 h

4: 100 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

5: 82 percent / pyridine / CH₂Cl₂ / 5 h / 0 °C

With pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00099a081