(S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate

Base Information

• Chemical Name: (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate
• CAS No.: 1072440-18-6
• Molecular Formula: C₃₈H₄₇NO₈
• Molecular Weight: 645.793
• Mol file: 1072440-18-6.mol

Synonyms:(S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate

Chemical Property of (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate

There total 2 articles about (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate 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: 28.0%

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) + (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol (93125-77-0) → (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate (1072440-18-6) + (S)-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate + C48H62N2O11

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Inert atmosphere;

DOI:10.1021/ol802009v

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) + (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol (93125-77-0) → (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate (1072440-18-6) + (S)-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Overall yield = 70 %;

DOI:10.1021/jo401044x

Reference yield: 89.0%

(S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate (1072440-18-6) → tert-butyl (3S,7S,8R,9R,10R,Z)-8,9-bis(benzyloxy)-10-(benzyloxymethyl)-7-hydroxy-2-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-3-ylcarbamate

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 35 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol802009v

upstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol