Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

Base Information

Chemical Name:Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester
CAS No.:332178-29-7
Molecular Formula:C₄₃H₄₅NO₆
Molecular Weight:671.833
Hs Code.:

Synonyms:Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

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Chemical Property of Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

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Technology Process of Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

There total 8 articles about Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl 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: 60.5%

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

: 332178-29-7
Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

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

Guidance literature:: (3R,4S,5S,6R)-6-[N-benzyl-N-(benzyloxycarbonyl)amino]-3,4,5-tris(benzyloxy)cycloheptene; With dimethylsulfide borane complex; In diethyl ether; at -30 - 0 ℃; for 18h;

With sodium hydroxide; dihydrogen peroxide; for 3h;
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

: 332178-29-7
Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 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

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

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

With chloro-trimethyl-silane; borane-THF; 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

: 332178-29-7
Benzyl-((1R,2S,3R,4R)-2,3,4-tris-benzyloxy-5-hydroxy-cycloheptyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: KHCO₃ / CH₂Cl₂; H₂O / 1.03 h

2.1: 93 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

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;
DOI:10.1021/jo020645c