(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

Base Information

• Chemical Name: (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
• CAS No.: 609817-41-6
• Molecular Formula: C₃₇H₆₇N₃O₅Si₂
• Molecular Weight: 690.127

Synonyms:

Chemical Property of (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

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-butyldimethylsilanyloxy)-9-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-2-methyltridec-4-enoic acid methyl ester

There total 10 articles about (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 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:

(3S)-4-(methoxymethoxy)-3-methylbutanal (112763-39-0) → (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 (609817-41-6)

Guidance literature:

Multi-step reaction with 11 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

9.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

10.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol / 0 °C

11.1: diethyl ether

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; 15-crown-5; dimethylboron bromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Wittig reaction / 9.1: Dess-Martin oxidation;

DOI:10.1021/ol035368q

Reference yield:

C10H19LiO2 (609817-34-7) → (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 (609817-41-6)

Guidance literature:

Multi-step reaction with 8 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

6.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

7.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol / 0 °C

8.1: diethyl ether

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; 15-crown-5; dimethylboron bromide; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol; 6.1: Dess-Martin oxidation;

DOI:10.1021/ol035368q

Reference yield:

(2S)-7-iodo-1-(methoxymethoxy)-2-methyl-4-heptene (609817-29-0) → (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 (609817-41-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: t-BuLi / diethyl ether / -78 °C

2.1: diethyl ether / 0.5 h / -78 °C

2.2: 86 percent / collidine / diethyl ether / -78 - 20 °C

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

3.2: pyridine / 20 °C

4.1: 14 percent / NaN₃; 15-crown-5; HMPA / 22 °C

5.1: 97 percent / collidine / -78 °C

6.1: 76 percent / Me₂BBr; Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

7.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

8.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol / 0 °C

9.1: diethyl ether

With 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; 15-crown-5; dimethylboron bromide; tert.-butyl lithium; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol; 7.1: Dess-Martin oxidation;

DOI:10.1021/ol035368q

upstream raw materials:

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

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

C₁₀H₁₉LiO₂

tert-Butyl-((Z)-(S)-7-methoxymethoxy-6-methyl-hept-3-enyloxy)-dimethyl-silane

Downstream raw materials:

stemonine

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