(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

Base Information

Chemical Name:(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one
CAS No.:609817-36-9
Molecular Formula:C₃₈H₇₀O₆Si₂
Molecular Weight:679.141
Hs Code.:

(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

Synonyms:(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

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Chemical Property of (Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

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Technology Process of (Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

There total 6 articles about (Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-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: 86.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 158587-49-6
(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

: 609817-34-7
C₁₀H₁₉LiO₂

: 609817-36-9
(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

Guidance literature:: (3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one; C₁₀H₁₉LiO₂; In diethyl ether; at -78 ℃; for 0.5h;

t-butyldimethylsiyl triflate; With 2,3,5-trimethyl-pyridine; In diethyl ether; at -78 - 20 ℃;
DOI:10.1021/ol035368q

Reference yield:

: 112763-37-8
(2R)-1-(methoxymethoxy)-2-methyl-3-(p-tolylsulfonyloxy)propane

: 609817-36-9
(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dimethylsulfoxide / 70 °C

2.1: DIBAL / diethyl ether / -78 - 20 °C

2.2: H₃O⁺ / diethyl ether

3.1: 85 percent / KHMDS / diethyl ether / -78 °C

4.1: TBAF / tetrahydrofuran / 0 - 20 °C

4.2: 80 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 0 °C

5.1: t-BuLi / diethyl ether / -78 °C

6.1: diethyl ether / 0.5 h / -78 °C

6.2: 86 percent / collidine / diethyl ether / -78 - 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; 3.1: Wittig reaction;
DOI:10.1021/ol035368q

Reference yield:

: 112763-38-9
(3S)-4-(methoxymethoxy)-3-methylbutyronitrile

: 609817-36-9
(Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIBAL / diethyl ether / -78 - 20 °C

1.2: H₃O⁺ / diethyl ether

2.1: 85 percent / KHMDS / diethyl ether / -78 °C

3.1: TBAF / tetrahydrofuran / 0 - 20 °C

3.2: 80 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 0 °C

4.1: t-BuLi / diethyl ether / -78 °C

5.1: diethyl ether / 0.5 h / -78 °C

5.2: 86 percent / collidine / diethyl ether / -78 - 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; 2.1: Wittig reaction;
DOI:10.1021/ol035368q