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

Base Information

• Chemical Name: 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
• CAS No.: 206272-19-7
• 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-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-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-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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: 98.0%

trichloroacetonitrile (545-06-2) + 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-glucopyranose → 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 (206272-19-7)

Guidance literature:

With caesium carbonate; In dichloromethane;

DOI:10.1055/s-2001-18109

Reference yield:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → 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 (206272-19-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-tetrazole / CH₂Cl₂

2: m-CPBA / CH₂Cl₂ / -20 °C

3: 94 percent / I₂; H₂O / tetrahydrofuran

4: 98 percent / Cs₂CO₃ / CH₂Cl₂

With 1H-tetrazole; water; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2001-18109

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-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate (206272-19-7)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / [Ir(cod)(MePh₂P)]PF₆ / tetrahydrofuran

2: pyridine / CH₂Cl₂

3: 83 percent / Me₂NH*BH₃; BF₃*OEt₂ / acetonitrile

4: 1H-tetrazole / CH₂Cl₂

5: m-CPBA / CH₂Cl₂ / -20 °C

6: 94 percent / I₂; H₂O / tetrahydrofuran

7: 98 percent / Cs₂CO₃ / CH₂Cl₂

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

DOI:10.1055/s-2001-18109

upstream raw materials:

trichloroacetonitrile

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

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

Downstream raw materials:

C₈₁H₈₈Cl₃N₆O₂₅P

C₆₀H₇₃Cl₆N₂O₁₈P

C₆₄H₇₇Cl₆N₂O₂₀P

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

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