(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

Base Information

Chemical Name:(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone
CAS No.:358972-73-3
Molecular Formula:C₄₃H₄₃NO₆
Molecular Weight:669.818
Hs Code.:

Synonyms:(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

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Chemical Property of (2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

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Technology Process of (2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

There total 7 articles about (2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone 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: 63.0%

: 358972-72-2
(3R,4S,5R,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene

: 358972-73-3
(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

: Benzyl-((1R,2R,3S,4R)-2,3,4-tris-benzyloxy-6-oxo-cycloheptyl)-carbamic acid benzyl ester

Guidance literature:: (3R,4S,5R,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene; With borane; In tetrahydrofuran; at -50 - 0 ℃;

With sodium hydroxide; dihydrogen peroxide; at 0 ℃;

With Dess-Martin periodane; In dichloromethane; at 20 ℃;
DOI:10.1039/b102353p

Reference yield:

: 358972-71-1
(3R,4S,5R,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)-1,8-nonadiene

: 358972-73-3
(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 83 percent / PhCH=RuCl₂(PCy₃)(CHNMesCH₂CH₂NMes) / CH₂Cl₂ / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / -40 - 0 °C

2.2: aqueous NaOH; hydrogen peroxide / tetrahydrofuran / 0 - 20 °C

2.3: 63 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With borane-THF; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 2.3: Dess-Martin oxidation;
DOI:10.1021/jo020645c

Reference yield:

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

: 358972-73-3
(2S,3R,4R,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: KHCO₃ / CH₂Cl₂; H₂O / 1.03 h

2.1: 83 percent / PhCH=RuCl₂(PCy₃)(CHNMesCH₂CH₂NMes) / CH₂Cl₂ / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 4 h / -40 - 0 °C

3.2: aqueous NaOH; hydrogen peroxide / tetrahydrofuran / 0 - 20 °C

3.3: 63 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With borane-THF; potassium hydrogencarbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; 3.3: Dess-Martin oxidation;
DOI:10.1021/jo020645c