(Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol

Base Information

• Chemical Name: (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol
• CAS No.: 609817-40-5
• Molecular Formula: C₃₂H₅₇N₃O₅Si
• Molecular Weight: 591.907
• Mol file: 609817-40-5.mol

Synonyms:(Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol

Chemical Property of (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol

There total 8 articles about (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-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: 14.0%

Methanesulfonic acid (Z)-(1R,7S)-1-{(1S,2R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pentyl}-8-methoxymethoxy-7-methyl-oct-4-enyl ester (609817-38-1) → {(R)-4-Benzyloxy-1-[(2R,3R,4S)-2-((Z)-(S)-7-methoxymethoxy-6-methyl-hept-3-enyl)-4-methyl-tetrahydro-furan-3-yl]-butoxy}-tert-butyl-dimethyl-silane + (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol (609817-40-5) + {(4R,5R,6S,12S)-(Z)-6-azido-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-enyloxymethyl}benzene (609817-39-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; at 22 ℃;

DOI:10.1021/ol035368q

Reference yield:

(2R)-1-(methoxymethoxy)-2-methyl-3-(p-tolylsulfonyloxy)propane (112763-37-8) → (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol (609817-40-5)

Guidance literature:

Multi-step reaction with 8 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

7.1: LiEt₃BH / tetrahydrofuran / -78 - 20 °C

7.2: pyridine / 20 °C

8.1: 14 percent / NaN₃; 15-crown-5; HMPA / 22 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; 3.1: Wittig reaction;

DOI:10.1021/ol035368q

Reference yield:

(3S)-4-(methoxymethoxy)-3-methylbutyronitrile (112763-38-9) → (Z)-(2S,3R,4S,10S)-4-Azido-3-[(R)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-11-methoxymethoxy-2,10-dimethyl-undec-7-en-1-ol (609817-40-5)

Guidance literature:

Multi-step reaction with 7 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

6.1: LiEt₃BH / tetrahydrofuran / -78 - 20 °C

6.2: pyridine / 20 °C

7.1: 14 percent / NaN₃; 15-crown-5; HMPA / 22 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; 2.1: Wittig reaction;

DOI:10.1021/ol035368q

upstream raw materials:

Methanesulfonic acid (Z)-(1R,7S)-1-{(1S,2R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pentyl}-8-methoxymethoxy-7-methyl-oct-4-enyl ester

(2R)-1-(methoxymethoxy)-2-methyl-3-(p-tolylsulfonyloxy)propane

(3S)-4-(methoxymethoxy)-3-methylbutyronitrile

(3S)-4-(methoxymethoxy)-3-methylbutanal

Downstream raw materials:

{(4R,5R,6S,12S)-(Z)-6-azido-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-enyloxymethyl}benzene

(Z)-(2S,8S,9R,10R)-8-Azido-13-benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-9-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tridec-4-enoic acid

(Z)-(2S,8S,9R,10R)-8-azido-13-benzyloxy-10-(tert-butyldimethylsilanyloxy)-9-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-2-methyltridec-4-enoic acid methyl ester

(Z)-(2S,8S,9R,10R)-8-Azido-13-benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-9-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tridec-4-en-1-ol