(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-yl acetate

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-yl acetate
CAS No.:1608472-98-5
Molecular Formula:C₃₆H₆₆O₇Si₃
Molecular Weight:695.172
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-yl acetate

Synonyms:(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-yl acetate

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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-yl acetate

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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-yl acetate

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-yl acetate 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: 93.0%

: 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

: 108-24-7
acetic anhydride

: 1608472-98-5
(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-yl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield: 93.0%

: C₃₄H₆₄O₆Si₃

: 108-24-7
acetic anhydride

: 1608472-98-5
(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-yl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; 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

: 1608472-98-5
(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-yl acetate

Guidance literature:: Multi-step reaction with 6 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

6.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

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