5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

Base Information

Chemical Name:5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose
CAS No.:118222-14-3
Molecular Formula:C₂₂H₃₁NO₆SSi
Molecular Weight:465.643
Hs Code.:

Synonyms:5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

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Chemical Property of 5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

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Technology Process of 5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

There total 2 articles about 5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose 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: 91.0%

: 118222-13-2
5-O-(tert-butyldimethylsilyl)-3-C-cyano-3-hydroxy-1,2-O-isopropylidene-α-D-xylo-pentofuranose

: 1005-56-7
phenylcarbonochloridothioate

: 118222-14-3
5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

Guidance literature:: With dmap; In acetonitrile; for 3h; Ambient temperature;
DOI:10.1016/S0040-4020(01)86194-9

Reference yield:

: 151-50-8
potassium cyanide

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 1005-56-7
phenylcarbonochloridothioate

: 118222-14-3
5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

Guidance literature:: potassium cyanide; 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose; In diethyl ether; water;

phenylcarbonochloridothioate; With dmap; In acetonitrile;
DOI:10.1016/S0008-6215(01)00132-X

Reference yield:

: 118222-14-3
5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

: 362600-09-7,779337-55-2
(3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / (n-Bu)3SnH; AIBN / toluene / 4 h / 70 °C

2: 65 percent / aq. AcOH / 24 h / 100 °C

3: 66 percent / H₂ / Pd/C / H₂O / 24 h / 20 °C / 10343 Torr

With 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic acid; palladium on activated charcoal; In water; toluene;
DOI:10.1016/S0008-6215(01)00132-X