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

Base Information

• Chemical Name: (2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane
• CAS No.: 471866-17-8
• Molecular Formula: C₃₄H₆₅NO₅SSi₂
• Molecular Weight: 656.131

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

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

Chemical Property:

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

There total 4 articles about (2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane 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: 68.0%

(2S,3R,4E)-1,3-bis(tert-butyldimethylsilyloxy)-2-(p-toluenesulfonylamino)-4-pentadecene (471866-16-7) → (2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane (471866-17-8) + (2S,3S,4S,5R)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 0 ℃; for 96h;

DOI:10.1271/bbb.66.1531

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane (471866-17-8)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 68 percent / dimethyldioxirane / acetone / 96 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1271/bbb.66.1531

Reference yield:

15-carbon-sphingosine (86555-28-4) → (2S,3S,4R,5S)-1,3-bis(tert-butyldimethylsilyloxy)-4,5-epoxy-2-(p-toluenesulfonylamino)pentadecane (471866-17-8)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 68 percent / dimethyldioxirane / acetone / 96 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1271/bbb.66.1531

upstream raw materials:

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

t-butyldimethylsiyl triflate

15-carbon-sphingosine

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

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