(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

Base Information

• Chemical Name: (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
• CAS No.: 609817-45-0
• Molecular Formula: C₃₆H₆₇N₃O₄Si₂
• Molecular Weight: 662.117
• Mol file: 609817-45-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 76.0%

{(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) → (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 (609817-45-0)

Guidance literature:

With dimethylboron bromide; triethylamine; In dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1021/ol035368q

Reference yield:

(3S)-4-(methoxymethoxy)-3-methylbutanal (112763-39-0) → (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 (609817-45-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / KHMDS / diethyl ether / -78 °C

2.1: TBAF / tetrahydrofuran / 0 - 20 °C

2.2: 80 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 0 °C

3.1: t-BuLi / diethyl ether / -78 °C

4.1: diethyl ether / 0.5 h / -78 °C

4.2: 86 percent / collidine / diethyl ether / -78 - 20 °C

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

5.2: pyridine / 20 °C

6.1: 14 percent / NaN₃; 15-crown-5; HMPA / 22 °C

7.1: 97 percent / collidine / -78 °C

8.1: 76 percent / Me₂BBr; Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; dimethylboron bromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; lithium triethylborohydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Wittig reaction;

DOI:10.1021/ol035368q

Reference yield:

C10H19LiO2 (609817-34-7) → (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 (609817-45-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethyl ether / 0.5 h / -78 °C

1.2: 86 percent / collidine / diethyl ether / -78 - 20 °C

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

2.2: pyridine / 20 °C

3.1: 14 percent / NaN₃; 15-crown-5; HMPA / 22 °C

4.1: 97 percent / collidine / -78 °C

5.1: 76 percent / Me₂BBr; Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; dimethylboron bromide; lithium triethylborohydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol035368q

upstream 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

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

(2S)-7-iodo-1-(methoxymethoxy)-2-methyl-4-heptene

C₁₀H₁₉LiO₂

Downstream raw materials:

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