(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

Base Information

Chemical Name:(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one
CAS No.:161985-50-8
Molecular Formula:C₃₄H₆₀O₇Si
Molecular Weight:608.932
Hs Code.:

(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

Synonyms:(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

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Chemical Property of (3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

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Technology Process of (3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

There total 17 articles about (3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one 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: 96.0%

: 161985-49-5
(3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one

: 161985-50-8
(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

Guidance literature:: With hydrogen; Wilkinson's catalyst; In benzene; for 16h; under 11250.9 Torr;
DOI:10.1016/0040-4039(94)02205-P

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 161985-50-8
(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) TiCl₄, i-Pr₂NEt / 1.) CH₂Cl₂, 0 deg C, 1 h; 2.) CH₂Cl₂, 0 deg C, 16 h

2: Me₃Al / CH₂Cl₂ / 20 h / -15 - 20 °C

3: tetrahydrofuran / 2 h / -78 °C

4: CeCl₃*7H₂O, NaBH₄ / ethanol / 1.5 h / -78 °C

5: 2,6-lutidine / tetrahydrofuran / 0.33 h / 0 °C

6: (CO₂H)2 / tetrahydrofuran; H₂O / 20 h / 20 °C

7: 1.) nBu₂BOTf, iPr₂NEt / 1.) CH₂Cl₂, -78 deg C, 2 h; 2.) CH₂Cl₂, -78 deg C to -25 deg C, 16 h

8: 96 percent / H₂ / (Ph₃P)3RhCl / benzene / 16 h / 11250.9 Torr

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; oxalic acid; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; water; benzene;
DOI:10.1016/0040-4039(94)02205-P

Reference yield:

: 116660-67-4,122330-69-2,149250-62-4,97848-38-9
(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal

: 161985-50-8
(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: TiCl₄ / CH₂Cl₂ / 0.17 h / -94 °C

2: TBAF / tetrahydrofuran / 0.5 h / 20 °C

3: PPTS / CH₂Cl₂ / 4 h / 20 °C

4: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 deg C, 4 h; 2.) pH=7 buffer, 10 min

5: 1.) nBu₂BOTf, iPr₂NEt / 1.) CH₂Cl₂, -78 deg C, 2 h; 2.) CH₂Cl₂, -78 deg C to -25 deg C, 16 h

6: 96 percent / H₂ / (Ph₃P)3RhCl / benzene / 16 h / 11250.9 Torr

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/0040-4039(94)02205-P