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

Base Information

• Chemical Name: 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
• CAS No.: 247158-45-8
• Molecular Formula: C₄₄H₅₅Cl₃NO₁₂P
• Molecular Weight: 927.253

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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: 91.0%

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) + allyl 6-O-benzyl-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-4-O-(1,5-dihydro-3-oxy-3H-2,4,3λ5-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (247158-45-8)

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

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8) → 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 (247158-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 25 °C

2.1: 70 percent / BH₃-Me₂NH; BF₃-OEt₂ / acetonitrile / 2 h / -20 - 25 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 0.17 h / 25 °C

3.2: 91 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / 25 °C

With 1H-tetrazole; dmap; dimethylamine borane; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; 1.1: Esterification / 2.1: Reduction / 3.1: Substitution / 3.2: Oxidation;

DOI:10.1246/bcsj.72.1857

Reference yield:

allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)decanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (247158-39-0) → 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 (247158-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / BH₃-Me₂NH; BF₃-OEt₂ / acetonitrile / 2 h / -20 - 25 °C

2.1: 1H-tetrazole / CH₂Cl₂ / 0.17 h / 25 °C

2.2: 91 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / 25 °C

With 1H-tetrazole; dimethylamine borane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; 1.1: Reduction / 2.1: Substitution / 2.2: Oxidation;

DOI:10.1246/bcsj.72.1857

upstream raw materials:

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

allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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

Downstream raw materials:

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-glucopyranose

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