(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

Base Information

Chemical Name:(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene
CAS No.:332178-28-6
Molecular Formula:C₄₃H₄₃NO₅
Molecular Weight:653.818
Hs Code.:

Synonyms:(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

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Chemical Property of (3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

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Technology Process of (3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

There total 7 articles about (3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene 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: 97.0%

: 358972-61-9
(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)-1,8-nonadiene

: 332178-28-6
(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

Guidance literature:: With Grubbs catalyst first generation; In dimethyl sulfoxide; at 20 ℃; for 4.5h;
DOI:10.1016/S0040-4039(00)02262-0

Reference yield:

: 85716-43-4
methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 332178-28-6
(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

Guidance literature:: Multi-step reaction with 3 steps

1.1: zinc; TMSCl / tetrahydrofuran / 40 °C / sonication

1.2: tetrahydrofuran / 1 h / 40 °C / sonication

1.3: tetrahydrofuran / 0.33 h / 40 °C / sonication

2.1: KHCO₃ / CH₂Cl₂; H₂O / 1.03 h

3.1: 93 percent / PhCH=RuCl₂(PCy₃)(CHNMesCH₂CH₂NMes) / CH₂Cl₂ / 20 °C

With chloro-trimethyl-silane; potassium hydrogencarbonate; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; 1.3: Barbier-type allylation;
DOI:10.1021/jo020645c

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 332178-28-6
(3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

Guidance literature:: Multi-step reaction with 2 steps

1: KHCO₃ / CH₂Cl₂; H₂O / 1.03 h

2: 93 percent / PhCH=RuCl₂(PCy₃)(CHNMesCH₂CH₂NMes) / CH₂Cl₂ / 20 °C

With potassium hydrogencarbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; water;
DOI:10.1021/jo020645c