Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester
• CAS No.: 207516-20-9
• Molecular Formula: C₃₀H₄₉NO₅
• Molecular Weight: 503.723

Synonyms:Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

Chemical Property of Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

Chemical Property:

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Technology Process of Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

There total 3 articles about Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester 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: 77.0%

benzoic acid anhydride (93-97-0) + N-tert-butyloxycarbonylsphingosine (116467-63-1) → Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester (207516-20-9)

Guidance literature:

With dmap; In dichloromethane; chemoselective reaction;

DOI:10.1055/s-0029-1217956

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester (207516-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaHCO₃

2: 55 percent / DMAP / CH₂Cl₂

With dmap; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/S0960-894X(98)00112-7

Reference yield:

D-erythro-sphingosine sulfate → Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester (207516-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaHCO₃

2: 55 percent / DMAP / CH₂Cl₂

With dmap; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/S0960-894X(98)00112-7

upstream raw materials:

benzoic acid anhydride

N-tert-butyloxycarbonylsphingosine

di-tert-butyl dicarbonate

Downstream raw materials:

(4S,5R)-4-{Bis-[1-(2-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester

tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate

Sphingosine-1-phosphate

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