ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

Base Information

Chemical Name:ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate
CAS No.:143842-51-7
Molecular Formula:C₃₉H₅₆F₂O₈SSi₂
Molecular Weight:779.103
Hs Code.:

Synonyms:ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

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Chemical Property of ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

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Technology Process of ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

There total 8 articles about ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate 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: 99.0%

: 124-63-0
methanesulfonyl chloride

: 143842-40-4,143857-18-5
ethyl (3S,4R,5S)-2,2-difluoro-3-hydroxy-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

: 143842-51-7
ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

Guidance literature:: With pyridine; at 22 ℃;
DOI:10.1021/ja00048a017

Reference yield:

: 143842-35-7
(2R,3S)-1,3-dihydroxy-2-(1-hexynyl)-4-<(p-bromobenzyl)oxy>butane

: 143842-51-7
ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine, H₂ / Pd/BaSO₄ / 20 h / 760 Torr

2: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, RT, 90 min

3: 81 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 48 h / Ambient temperature

4: 1.) O₃, MeOH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 3 h

5: 47.2 percent / Zn, 1,2-dibromoethane, chlorotrimethylsilane / tetrahydrofuran / 3 h / Ambient temperature

6: 99 percent / pyridine / 22 °C

With pyridine; methanol; dmap; chloro-trimethyl-silane; dimethylsulfide; hydrogen; sodium hydride; ozone; ethylene dibromide; triethylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja00048a017

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 143842-51-7
ethyl (3S,4R,5S)-2,2-difluoro-3-(mesyloxy)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-<(tert-butyldimethylsilyl)oxy>-6-(benzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 48 h / Ambient temperature

2: 1.) O₃, MeOH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 3 h

3: 47.2 percent / Zn, 1,2-dibromoethane, chlorotrimethylsilane / tetrahydrofuran / 3 h / Ambient temperature

4: 99 percent / pyridine / 22 °C

With pyridine; methanol; dmap; chloro-trimethyl-silane; dimethylsulfide; ozone; ethylene dibromide; triethylamine; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja00048a017