(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Base Information

Chemical Name:(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one
CAS No.:1268687-88-2
Molecular Formula:C₄₆H₈₄O₇Si₂
Molecular Weight:805.34
Hs Code.:

(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Synonyms:(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

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Chemical Property of (5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

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Technology Process of (5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

There total 15 articles about (5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-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: 61.0%

: 1268687-73-5
C₁₉H₃₆O₂Si

: 1268687-74-6
(5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

: 1268687-88-2
(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Guidance literature:: (5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one; With lithium diisopropyl amide; In tetrahydrofuran; at -50 ℃;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran;

C₁₉H₃₆O₂Si; optical yield given as %de; Further stages;
DOI:10.1002/ejoc.201101129

Reference yield: 61.0%

: 1268687-73-5
C₁₉H₃₆O₂Si

: 1268687-87-1
(6S,7S,8S,Z)-4-ethyliden-6-methoxy-8-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,5,5,7,10,10,11,11-nonamethyl-3,9-dioxa-2,10-disiladodecane

: 1268687-88-2
(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Guidance literature:: With calcium hydride; boron trifluoride diethyl etherate; In dichloromethane; at -95 - -78 ℃; for 3.75h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201005605

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1268687-88-2
(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / -10 - 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / 5 h / 0 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: calcium hydride; boron trifluoride diethyl etherate / dichloromethane / 3.75 h / -95 - -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium borohydride; calcium hydride; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama reaction;
DOI:10.1002/anie.201005605