6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate
• CAS No.: 230966-85-5
• Molecular Formula: C₅₄H₇₉Cl₆N₂O₁₃P
• Molecular Weight: 1207.92

Synonyms:6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Chemical Property of 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

There total 3 articles about 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-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: 99.0%

trichloroacetonitrile (545-06-2) + 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose → 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate (230966-85-5)

Guidance literature:

With caesium carbonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1246/bcsj.72.1377

Reference yield:

allyl 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (230966-81-1) → 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate (230966-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / [Ir(cod)(MePh₂P)2]PF₆ / CHCl₃ / 0.33 h / 20 °C

2: 1.57 g / iodine; water / tetrahydrofuran / 0.33 h

3: 99 percent / Cs₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With water; hydrogen; iodine; caesium carbonate; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; dichloromethane; chloroform; 1: Isomerization / 2: Hydrolysis / 3: Addition;

DOI:10.1246/bcsj.72.1377

Reference yield:

(R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-6-[((E)-propenyl)oxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester → 6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate (230966-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.57 g / iodine; water / tetrahydrofuran / 0.33 h

2: 99 percent / Cs₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With water; iodine; caesium carbonate; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Addition;

DOI:10.1246/bcsj.72.1377

upstream raw materials:

trichloroacetonitrile

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

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