(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

Base Information

Chemical Name:(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate
CAS No.:1399679-99-2
Molecular Formula:C₅₀H₇₄O₆Si₂
Molecular Weight:827.305
Hs Code.:

(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

Synonyms:(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

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Chemical Property of (3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

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Technology Process of (3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

There total 16 articles about (3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate 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: 75.0%

: 1399680-27-3
(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl 3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

: 1399679-99-2
(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 23 ℃; for 1h; pH=7;
DOI:10.1021/ol301886g

Reference yield:

: 556-82-1
3-methyl-2-buten-1-ol

: 1399679-99-2
(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 23 °C

2.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane; benzene / 48 h / Inert atmosphere

3.1: n-butyllithium; potassium tert-butylate / hexane / 0.75 h / -78 - -50 °C / Inert atmosphere

3.2: 0.75 h / Inert atmosphere

4.1: dmap / toluene / 0 - 23 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; n-butyllithium; potassium tert-butylate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; salicylic acid; In hexane; dichloromethane; toluene; benzene; 2.1: |Riley Selenium Dioxide Oxidation;
DOI:10.1021/ol301886g

Reference yield:

: 141561-63-9
(((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene

: 1399679-99-2
(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane; benzene / 48 h / Inert atmosphere

2.1: n-butyllithium; potassium tert-butylate / hexane / 0.75 h / -78 - -50 °C / Inert atmosphere

2.2: 0.75 h / Inert atmosphere

3.1: dmap / toluene / 0 - 23 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; n-butyllithium; potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; salicylic acid; In hexane; dichloromethane; toluene; benzene; 1.1: |Riley Selenium Dioxide Oxidation;
DOI:10.1021/ol301886g