(2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene

Base Information

• Chemical Name: (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene
• CAS No.: 471866-16-7
• Molecular Formula: C₃₄H₆₅NO₄SSi₂
• Molecular Weight: 640.131
• Mol file: 471866-16-7.mol

Synonyms:(2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene

Chemical Property of (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene

There total 3 articles about (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,3R,4E)-2-amino-1,3-bis(tert-butyldimethylsilyloxy)-4-pentadecene (471866-15-6) → (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene (471866-16-7)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1271/bbb.66.1531

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene (471866-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 0 - 20 °C

2: 90 percent / pyridine / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1271/bbb.66.1531

Reference yield:

15-carbon-sphingosine (86555-28-4) → (2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene (471866-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 0 - 20 °C

2: 90 percent / pyridine / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1271/bbb.66.1531

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3R,4E)-2-amino-1,3-bis(tert-butyldimethylsilyloxy)-4-pentadecene

t-butyldimethylsiyl triflate

15-carbon-sphingosine

Downstream raw materials:

(2S,3S,4R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecanol

(2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane