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

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Chemical Name:(2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-(O-isopropylidene)octane-1,2,4,6,8-pentol
CAS No.:120341-86-8
Molecular Formula:C₃₃H₄₈O₅Si
Molecular Weight:552.827
Hs Code.:

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

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Chemical Property of (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-(O-isopropylidene)octane-1,2,4,6,8-pentol

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Technology Process of (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-(O-isopropylidene)octane-1,2,4,6,8-pentol

There total 10 articles about (2S,4S,6S)-8-(O-tert-butyldiphenylsilyl)-4,6-(O-cyclohexylidene)-1,2-(O-isopropylidene)octane-1,2,4,6,8-pentol 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: 93.0%

: 933-40-4
cycloxexanone dimethyl ketal

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

: 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

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; for 4h; Ambient temperature;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 120409-53-2
2-((2S)-2,3-O-isopropylidene-2,3-dihydroxypropyl)-1,3-dithiane

: 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

Guidance literature:: Multi-step reaction with 4 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

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