(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

Base Information

Chemical Name:(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol
CAS No.:144402-31-3
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

Synonyms:(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

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Chemical Property of (2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

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Technology Process of (2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

There total 7 articles about (2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol 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: 100.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 164031-24-7
(S)-2-[(4R,6S)-6-((S)-2,2-Diphenyl-[1,3]dioxolan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol

: 144402-31-3
(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;
DOI:10.1016/0040-4020(95)00214-S

Reference yield:

: 81380-10-1
(2S,3S)-4-benzyloxy-1,2-epoxy-3-methylbutane

: 144402-31-3
(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, -30 deg C, 2 h, 2.) THF, -25 deg C, 15 h

2: 88 percent / MeI, CaCO₃, H₂O / acetonitrile / 16 h

3: 95 percent / NaBH₄, Et₂BOMe / tetrahydrofuran; methanol / 3 h / -78 °C

4: 90 percent / PPTS / CH₂Cl₂ / 0.33 h

5: 81 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h

6: 99 percent / imidazole / dimethylformamide / 3.5 h

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; water; hydrogen; pyridinium p-toluenesulfonate; calcium carbonate; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3987/COM-92-6041

Reference yield:

: 144402-29-9
(2S,4S,6R,7S)-8-benzyloxy-1,2-O-diphenylmethylidene-7-methyloctane-1,2,4,6-tetrol

: 144402-31-3
(2S,4S,6R,7S)-8-<(tert-butyldimethylsilyl)oxy>-1,2-O-diphenylmethylidene-4,6-O-isopropylidene-7-methyloctane-1,2,4,6-tetrol

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / PPTS / CH₂Cl₂ / 0.33 h

2: 81 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h

3: 99 percent / imidazole / dimethylformamide / 3.5 h

With 1H-imidazole; hydrogen; pyridinium p-toluenesulfonate; palladium dihydroxide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.3987/COM-92-6041