(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Base Information

Chemical Name:(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol
CAS No.:117097-27-5
Molecular Formula:C₂₂H₃₅NO₆Si
Molecular Weight:437.608
Hs Code.:

Synonyms:(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

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Technology Process of (+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

There total 9 articles about (+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol 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: 88.0%

: 117097-26-4
(+)-(2R,3R,4S)-5-benzyloxycarbonylamino-4-(t-butyldimethylsilyloxy)-2,3-(isopropylidenedioxy)-1-pentanol

: 117097-27-5
(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja00229a069

Reference yield: 88.0%

: 117097-25-3
5-N-(benzyloxycarbonyl)-4-O-(t-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-L-1,5-ribonolactam

: 117097-27-5
(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1246/bcsj.65.978

Reference yield:

: 117097-24-2
5-azido-5-deoxy-2,3-O-isopropylidene-L-ribono-1,4-lactone

: 117097-27-5
(+)-(2S,3S,4R,5S)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / H₂ / Raney Ni / methanol

2: 1.) imidazole, 2.) NaH / DMF

3: 70 percent / NaBH₄ / ethanol

4: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; nickel; In methanol; ethanol; dichloromethane;
DOI:10.1021/ja00229a069