(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

Base Information

Chemical Name:(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol
CAS No.:1643478-29-8
Molecular Formula:C₃₃H₆₄O₆Si₂
Molecular Weight:613.039
Hs Code.:

Synonyms:(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

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Chemical Property of (3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

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Technology Process of (3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

There total 14 articles about (3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-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: 86.0%

: 1643478-27-6
(3R,5R,6R,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecan-4-one

: 1643478-29-8
(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

Guidance literature:: With benzo[1,3,2]dioxaborole; In tetrahydrofuran; for 12h; Inert atmosphere; Cooling;
DOI:10.1039/c4ob00250d

Reference yield:

: 1643478-27-6
(3R,5R,6R,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecan-4-one

: (3R,4R,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

: 1643478-29-8
(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; dichloromethane; at -40 ℃; for 6h; Overall yield = 40 %;
DOI:10.1039/c4ob00250d

Reference yield:

: 916501-75-2
2-<(benzyloxy)-methyl>butyraldehyde

: 1643478-29-8
(3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 0 °C / Inert atmosphere

2.1: palladium on activated charcoal; hydrogen / 20 °C / 760.05 Torr

3.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere; Heating

3.2: Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

5.2: 14 h / -78 - -25 °C / Inert atmosphere

6.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 12 h / Inert atmosphere; Cooling

With palladium on activated charcoal; dicyclohexylboron chloride; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: |Grignard Reaction;
DOI:10.1039/c4ob00250d