(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

Base Information

Chemical Name:(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol
CAS No.:120341-88-0
Molecular Formula:C₃₀H₄₂O₄Si
Molecular Weight:494.747
Hs Code.:

Synonyms:(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

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Chemical Property of (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

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Technology Process of (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

There total 12 articles about (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol 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: 94.0%

: 131522-39-9
Toluene-4-sulfonic acid (S)-3-{(2R,4S)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1,5-dioxa-spiro[5.5]undec-2-yl}-2-hydroxy-propyl ester

: 120341-88-0
(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

Guidance literature:: With methanol; potassium hydride; In methanol; diethyl ether; at 0 ℃; for 1h;
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

: 120341-88-0
(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

Guidance literature:: Multi-step reaction with 7 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

6: pyridine / 3 h / 0 °C

7: KH / diethyl ether; methanol / 0.33 h / 0 °C

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

Reference yield:

: 120341-84-6
(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-1,2-(O-isopropylidene)-octane-1,2,4,6,8-pentol

: 120341-88-0
(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-epoxyoctane-4,6,8-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / PPTS / CH₂Cl₂ / 7 h

2: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C

3: pyridine / 3 h / 0 °C

4: KH / diethyl ether; methanol / 0.33 h / 0 °C

With pyridine; pyridinium p-toluenesulfonate; potassium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid;
DOI:10.1016/S0040-4039(00)82885-3