(S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol

Base Information

• Chemical Name: (S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol
• CAS No.: 111467-06-2
• Molecular Formula: C₃₇H₄₁NO₄
• Molecular Weight: 563.737

Synonyms:(S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol

Chemical Property of (S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol

Chemical Property:

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Technology Process of (S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol

There total 1 articles about (S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-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: 66.0%

(2S,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidine-2-carbaldehyde + allyl-trimethyl-silane (762-72-1) → (S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol (111467-06-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo00233a045

Reference yield:

(S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol (111467-06-2) → Acetic acid (S)-1-((2R,3R,4R,5R)-1-benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-4-hydroxy-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: borane, Me₂S, H₂O₂ / tetrahydrofuran

With dimethylsulfide; borane; dihydrogen peroxide; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00233a045

Reference yield:

(S)-1-((2R,3R,4R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-but-3-en-1-ol (111467-06-2) → Methanesulfonic acid (S)-3-((2R,3R,4R,5R)-1-benzyl-3,4,5-tris-benzyloxy-piperidin-2-yl)-3-hydroxy-propyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) EtOH

2: Et₃N / CH₂Cl₂

With sodium tetrahydroborate; ozone; triethylamine; In dichloromethane;

DOI:10.1021/jo00233a045

upstream raw materials:

allyl-trimethyl-silane

Downstream raw materials:

6-epi-castanospermine

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