allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Chemical Name:allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:247158-42-5
Molecular Formula:C₃₆H₄₈Cl₃NO₉
Molecular Weight:745.137
Hs Code.:

Synonyms:allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Chemical Property of allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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Technology Process of allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 2 articles about allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 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: 70.0%

: 247158-39-0
allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 247158-42-5
allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With dimethylamine borane; boron trifluoride diethyl etherate; In acetonitrile; at -20 - 25 ℃; for 2h;
DOI:10.1246/bcsj.72.1857

Reference yield:

: 183388-21-8
allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 247158-42-5
allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 25 °C

2: 70 percent / BH₃-Me₂NH; BF₃-OEt₂ / acetonitrile / 2 h / -20 - 25 °C

With dmap; dimethylamine borane; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; 1: Esterification / 2: Reduction;
DOI:10.1246/bcsj.72.1857

Reference yield: 91.0%

: 82372-35-8
N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine

: 247158-42-5
allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 247158-45-8
allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxy-3H-2,4,3λ⁵-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine; allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside; With 1H-tetrazole; In dichloromethane; at 25 ℃; for 0.166667h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 0.333333h;
DOI:10.1246/bcsj.72.1857