(2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol

Base Information

• Chemical Name: (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol
• CAS No.: 134485-33-9
• Molecular Formula: C₁₉H₂₃N₃O₄
• Molecular Weight: 357.409
• Mol file: 134485-33-9.mol

Synonyms:(2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol

Chemical Property of (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol

There total 6 articles about (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol 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:

5,5-Dibenzyloxy-2E-penten-1-ol (134485-31-7) → (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol (134485-33-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / tBuOOH, Ti(OiPr)4, (-)-diethyl tartrate ((-)-DET), 4-A sieves / CH₂Cl₂ / -20 °C

2: Ti(OiPr)4, Me₃SiN₃ / benzene

With titanium(IV) isopropylate; tert.-butylhydroperoxide; trimethylsilylazide; 4 A molecular sieve; (-)-diethyl tartrate; In dichloromethane; benzene;

DOI:10.1021/ja00013a088

Reference yield:

3,3-dibenzyloxypropanal (134485-38-4) → (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol (134485-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran

2: diisobutylaluminum hydride (DIBAL-H) / diethyl ether / -78 °C

3: 91 percent / tBuOOH, Ti(OiPr)4, (-)-diethyl tartrate ((-)-DET), 4-A sieves / CH₂Cl₂ / -20 °C

4: Ti(OiPr)4, Me₃SiN₃ / benzene

With titanium(IV) isopropylate; tert.-butylhydroperoxide; trimethylsilylazide; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00013a088

Reference yield:

(E)-5,5-Bis-benzyloxy-pent-2-enoic acid ethyl ester (134485-39-5) → (2S,3S)-3-Azido-5,5-bis-benzyloxy-pentane-1,2-diol (134485-33-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminum hydride (DIBAL-H) / diethyl ether / -78 °C

2: 91 percent / tBuOOH, Ti(OiPr)4, (-)-diethyl tartrate ((-)-DET), 4-A sieves / CH₂Cl₂ / -20 °C

3: Ti(OiPr)4, Me₃SiN₃ / benzene

With titanium(IV) isopropylate; tert.-butylhydroperoxide; trimethylsilylazide; 4 A molecular sieve; diisobutylaluminium hydride; (-)-diethyl tartrate; In diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00013a088

upstream raw materials:

[(2R,3R)-3-(2,2-Bis-benzyloxy-ethyl)-oxiranyl]-methanol

5,5-Dibenzyloxy-2E-penten-1-ol

3,3-dibenzyloxypropanal

ethyl-3,3-di(benzyl)oxypropanoate

Downstream raw materials:

3'-azido-2',3'-deoxythymidine

C₃₃H₃₁N₃O₆