6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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: 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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.: 192444-70-5
• Molecular Formula: C₄₇H₅₉Cl₆N₂O₁₂P
• Molecular Weight: 1087.68

Synonyms:6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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:

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Technology Process of 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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 8 articles about 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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: 100.0%

trichloroacetonitrile (545-06-2) + 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose → 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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 (192444-70-5)

Guidance literature:

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

DOI:10.1246/bcsj.70.1441

Reference yield:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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 (192444-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-tetrazole / CH₂Cl₂ / 0.83 h / -20 - 20 °C

2: 311 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.67 h / -20 °C

3: 88 percent / hydrogen; iodine; water / [Ir(cod)(MePh₂P)2]PF₆ / tetrahydrofuran / 0.67 h / 20 °C

4: 100 percent / Cs₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; water; hydrogen; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; dichloromethane; 1: phosphitylation / 2: Oxidation / 3: deallylation / 4: Addition;

DOI:10.1246/bcsj.70.1441

Reference yield:

allyl 4,6-O-benzylidene-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (172371-05-0) → 6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-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 (192444-70-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / sodium cyanotrihydroborate; hydrogen chloride / tetrahydrofuran / 0.17 h

2: 1H-tetrazole / CH₂Cl₂ / 0.83 h / -20 - 20 °C

3: 311 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.67 h / -20 °C

4: 88 percent / hydrogen; iodine; water / [Ir(cod)(MePh₂P)2]PF₆ / tetrahydrofuran / 0.67 h / 20 °C

5: 100 percent / Cs₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; hydrogenchloride; water; hydrogen; iodine; sodium cyanoborohydride; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; dichloromethane; 1: Ring cleavage / 2: phosphitylation / 3: Oxidation / 4: deallylation / 5: Addition;

DOI:10.1246/bcsj.70.1441

upstream raw materials:

trichloroacetonitrile

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

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

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

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