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

Base Information

• Chemical Name: {(4R,5R,6S,12S)-(Z)-6-azido-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-enyloxymethyl}benzene
• CAS No.: 609817-39-2
• Molecular Formula: C₃₈H₇₁N₃O₅Si₂
• Molecular Weight: 706.17
• Mol file: 609817-39-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about {(4R,5R,6S,12S)-(Z)-6-azido-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-enyloxymethyl}benzene 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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (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 2,3,5-trimethyl-pyridine; at -78 ℃;

DOI:10.1021/ol035368q

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) → {(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:

Multi-step reaction with 9 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

9.1: 97 percent / collidine / -78 °C

With 2,3,5-trimethyl-pyridine; 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

upstream raw materials:

t-butyldimethylsiyl triflate

(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

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

Downstream raw materials:

(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

stemonine

(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-enoic acid