tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate

Base Information

• Chemical Name: tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate
• CAS No.: 1072440-17-5
• Molecular Formula: C₃₆H₄₃NO₈
• Molecular Weight: 617.739
• Mol file: 1072440-17-5.mol

Synonyms:tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate

Chemical Property of tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate

There total 3 articles about tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate 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: 94.0%

(S)-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate → tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate (1072440-17-5)

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 15h; Inert atmosphere;

DOI:10.1021/ol802009v

Reference yield:

tert-butyl (3S,7S,Z)-2-oxo-7-((1R,3R)-1,2,4-tris(benzyloxy)-3-(tert-butyldimethylsilyloxy)butyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate (1072440-26-6) → tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate (1072440-17-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.333333h; 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) → tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate (1072440-17-5) + C36H43NO8

Guidance literature:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid; (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane;

DOI:10.1021/jo401044x

upstream raw materials:

tert-butyl (3S,7S,Z)-2-oxo-7-((1R,3R)-1,2,4-tris(benzyloxy)-3-(tert-butyldimethylsilyloxy)butyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate

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

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

Downstream raw materials:

(2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate

tert-butyl (2R,3R,4S,4aS,7S,9aR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-6-oxooctahydro-2H-pyrano[3,2-b]oxepin-7-ylcarbamate