allyl 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)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 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)-α-D-glucopyranoside
• CAS No.: 192444-68-1
• Molecular Formula: C₄₈H₆₃Cl₃NO₁₂P
• Molecular Weight: 983.36

Synonyms:allyl 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)-α-D-glucopyranoside

Chemical Property of allyl 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)-α-D-glucopyranoside

Chemical Property:

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Technology Process of allyl 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)-α-D-glucopyranoside

There total 6 articles about allyl 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)-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:

(S)-3-Benzyloxy-tetradecanoic acid (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 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)-α-D-glucopyranoside (192444-68-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 0.666667h;

DOI:10.1246/bcsj.70.1441

Reference yield:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → allyl 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)-α-D-glucopyranoside (192444-68-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1246/bcsj.70.1441

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8) → allyl 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)-α-D-glucopyranoside (192444-68-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 94 percent / sodium cyanotrihydroborate; hydrogen chloride / tetrahydrofuran / 0.17 h

3: 1H-tetrazole / CH₂Cl₂ / 0.83 h / -20 - 20 °C

4: 311 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.67 h / -20 °C

With 1H-tetrazole; hydrogenchloride; dmap; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: Ring cleavage / 3: phosphitylation / 4: Oxidation;

DOI:10.1246/bcsj.70.1441

upstream raw materials:

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

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

Downstream raw materials:

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

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