allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS No.: 206272-15-3
• Molecular Formula: C₃₁H₃₅Cl₃NO₁₂P
• Molecular Weight: 750.951

Synonyms:allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property of allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 5 articles about allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-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:

Carbonic acid allyl ester (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-5-(1,5-dihydro-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester → allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-15-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at -20 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-tetrazole / 1,2-dichloro-ethane / 0.25 h / 20 °C

2: 3.24 g / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 0.33 h / -20 °C

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; 1: phosphitylation / 2: Oxidation;

DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside → allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / pyridine; DMAP / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C

2: 90 percent / BH₃*Me₂NH; BF₃*Et₂O / acetonitrile / 1.5 h / 0 °C

3: 1H-tetrazole / 1,2-dichloro-ethane / 0.25 h / 20 °C

4: 3.24 g / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 0.33 h / -20 °C

With pyridine; 1H-tetrazole; dmap; dimethylamine borane; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; acetonitrile; 1: Acylation / 2: Ring cleavage / 3: phosphitylation / 4: Oxidation;

DOI:10.1016/S0040-4020(98)00133-1

upstream raw materials:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine

allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Downstream raw materials:

C₆₄H₇₇Cl₆N₂O₂₀P

C₆₀H₇₃Cl₆N₂O₁₈P

allyl 6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-4-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

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