(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

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Chemical Name:(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol
CAS No.:120341-87-9
Molecular Formula:C₃₀H₄₄O₅Si
Molecular Weight:512.762
Hs Code.:

Synonyms:(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

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Chemical Property of (S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

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Technology Process of (S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

There total 10 articles about (S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol 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: 42.0%

: 120341-86-8
(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-(O-isopropylidene)octane-1,2,4,6,8-pentol

: 120341-87-9
(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

Guidance literature:: With acetic acid; In tetrahydrofuran; at -5 ℃; for 48h;
DOI:10.1248/cpb.38.2574

Reference yield:

: 125975-53-3,147220-48-2,116996-54-4
(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

: 120341-87-9
(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, -20 deg C, 2 h, 2.) 17 h

2: 78 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

3: LiAlH₄, LiI / diethyl ether / 0.5 h / -100 °C

4: 93 percent / PPTS / CH₂Cl₂ / 7 h

5: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C

With 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; silver nitrate; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(00)82885-3

Reference yield:

: 120341-82-4
(2S,6S)-8-(O-tert-butyldiphenylsilyl)-1,2-(O-isopropylidene)-4-(trimethylenedithio)octane-1,2,6,8-tetrol

: 120341-87-9
(S)-3-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-propane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / NBS, AgNO₃, 2,6-lutidine / H₂O; acetonitrile / 0.12 h

2: LiAlH₄, LiI / diethyl ether / 0.5 h / -100 °C

3: 93 percent / PPTS / CH₂Cl₂ / 7 h

4: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C

With 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; silver nitrate; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(00)82885-3