(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

Base Information

Chemical Name:(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol
CAS No.:1608473-05-7
Molecular Formula:C₂₉H₄₈O₈Si
Molecular Weight:552.781
Hs Code.:

Synonyms:(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

There total 20 articles about (5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-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: 89.0%

: 1608473-12-6
(5S,6S,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-one

: 1608473-05-7
(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

: (5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -78 ℃; for 8h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield:

: (-)-(2E)-(4S)-ethyl 4-(p-methoxybenzyl)oxy-2-pentenoate

: 1608473-05-7
(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

: (5S,6R,7R,10S)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Inert atmosphere; Molecular sieve

2.2: 8 h / Inert atmosphere

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

4.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

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

7.2: 1 h / -78 - 0 °C / Inert atmosphere

8.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: 2 h / -78 °C / Inert atmosphere

9.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

10.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / toluene; tetrahydrofuran / 8 h / -78 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; dmap; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; dimethyl sulfide borane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 2.1: |Sharpless Asymmetric Epoxidation / 2.2: |Sharpless Allylic Amination;
DOI:10.1002/ejoc.201301215

Reference yield:

: 1608473-16-0
(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

: 1608473-05-7
(5S,6R,7R,10R)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

: (5S,6R,7R,10S)-10-allyl-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-6-(methoxymethoxy)-12,12,13,13-tetramethyl-2,4,11-trioxa-12-silatetradec-8-yn-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

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

3.2: 1 h / -78 - 0 °C / Inert atmosphere

4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

6.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / toluene; tetrahydrofuran / 8 h / -78 °C / Inert atmosphere

With dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfide borane; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1002/ejoc.201301215