(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

Base Information

Chemical Name:(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol
CAS No.:1608472-97-4
Molecular Formula:C₃₄H₆₄O₆Si₃
Molecular Weight:653.135
Hs Code.:

(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

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Chemical Property of (5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

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Technology Process of (5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

There total 9 articles about (5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol 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:

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 1608472-97-4
(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

: C₃₄H₆₄O₆Si₃

Guidance literature:: tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 0.583333h; Inert atmosphere;

In tetrahydrofuran; hexane; at -78 ℃; for 2h; Overall yield = 1.10 g; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield:

: 1608472-90-7
C₂₅H₄₆O₅Si₂

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 1608472-97-4
(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

: 6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

Guidance literature:: tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 0.583333h; Inert atmosphere;

C₂₅H₄₆O₅Si₂; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Overall yield = 1.1 g; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield:

: 1608472-93-0
((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol

: 1608472-97-4
(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / water; tert-butyl alcohol / 15 h / 70 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol / 0.5 h / -15 °C / Inert atmosphere

4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 0 °C / Inert atmosphere

5.1: n-butyllithium / hexane; tetrahydrofuran / 0.58 h / -78 - -20 °C / Inert atmosphere

5.2: 2 h / -78 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/ejoc.201301215