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

Base Information

• Chemical Name: 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 400843-71-2
• Molecular Formula: C₃₀H₃₁Cl₆N₂O₁₂P
• Molecular Weight: 855.274

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate 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:

trichloroacetonitrile (545-06-2) + 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose → 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate (400843-71-2)

Guidance literature:

With 4 A molecular sieve; caesium carbonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1246/bcsj.76.485

Reference yield:

allyl 4,6-O-benzylidene-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-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate (400843-71-2)

Guidance literature:

Multi-step reaction with 7 steps

1: (1,5-cyclooctadiene)[bis(MePh₂P)]iridium⁽¹⁺⁾*PF₆^(1-); H₂ / tetrahydrofuran / 1 h / 20 °C

2: 37.1 g / pyridine / CH₂Cl₂ / 0 - 20 °C

3: 68 percent / Me₂NH*BH₃; Et₂O*BF₃ / acetonitrile / 2 h / 0 °C

4: 1H-tetrazole / 1,2-dichloro-ethane / 0.67 h / -20 - 20 °C

5: 15.4 g / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 0.5 h

6: 86 percent / I₂; water / tetrahydrofuran / 1 h / 20 °C

7: molecular sieves 4 Angstroem; Cs₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-tetrazole; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; dimethylamine borane; 4 A molecular sieve; boron trifluoride diethyl etherate; water; hydrogen; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1246/bcsj.76.485

Reference yield:

{(4aR,6S,7R,8R,8aS)-8-Hydroxy-2-phenyl-6-[((E)-propenyl)oxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid 2,2,2-trichloro-ethyl ester → 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphophepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate (400843-71-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 37.1 g / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 68 percent / Me₂NH*BH₃; Et₂O*BF₃ / acetonitrile / 2 h / 0 °C

3: 1H-tetrazole / 1,2-dichloro-ethane / 0.67 h / -20 - 20 °C

4: 15.4 g / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 0.5 h

5: 86 percent / I₂; water / tetrahydrofuran / 1 h / 20 °C

6: molecular sieves 4 Angstroem; Cs₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-tetrazole; dimethylamine borane; 4 A molecular sieve; boron trifluoride diethyl etherate; water; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1246/bcsj.76.485

upstream raw materials:

trichloroacetonitrile

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

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

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

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