(2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol
• CAS No.: 1416052-09-9
• Molecular Formula: C₄₀H₆₉NO₂Si₂
• Molecular Weight: 652.164

Synonyms:(2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

Chemical Property of (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

There total 3 articles about (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-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: 88.0%

(2S,3R,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol (1416052-08-8) → (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol (1416052-09-9)

Guidance literature:

(2S,3R,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol; With trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 17h;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1271/bbb.120333

Reference yield:

(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol (916159-70-1) → (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol (1416052-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-dimethylpyridine / 0.25 h / 0 °C

2.1: trimethylphosphane / tetrahydrofuran / 17 h / 20 °C

2.2: 2 h / 20 °C

With 2,6-dimethylpyridine; trimethylphosphane; In tetrahydrofuran;

DOI:10.1271/bbb.120333

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol (1416052-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-dimethylpyridine / 0.25 h / 0 °C

2.1: trimethylphosphane / tetrahydrofuran / 17 h / 20 °C

2.2: 2 h / 20 °C

With 2,6-dimethylpyridine; trimethylphosphane; In tetrahydrofuran;

DOI:10.1271/bbb.120333

upstream raw materials:

(2S,3R,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol

t-butyldimethylsiyl triflate

Downstream raw materials:

(2S,3R,4E)-2-[(30'-acetoxy)triacontanamido]-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

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