allyl 6-O-benzyl-3-O-[(R)-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-[(R)-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.: 192196-07-9
• Molecular Formula: C₄₈H₆₃Cl₃NO₁₂P
• Molecular Weight: 983.36
• Mol file: 192196-07-9.mol

Synonyms:allyl 6-O-benzyl-3-O-[(R)-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-[(R)-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 6-O-benzyl-3-O-[(R)-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-[(R)-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:

(R)-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-[(R)-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 (192196-07-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 0.0833333h;

DOI:10.1246/bcsj.70.1435

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (172490-46-9) → allyl 6-O-benzyl-3-O-[(R)-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 (192196-07-9)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogen chloride / 0.33 h / Heating

2: 12.3 g / (+)-camphor-10-sulfonic acid / tetrahydrofuran / 3 h / Heating

3: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

4: 74 percent / sodium cyanotrihydroborate; hydrogen chloride / tetrahydrofuran / 1 h / 25 °C

5: 1H-tetrazole / CH₂Cl₂ / 0.33 h / 20 °C

6: 894 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.08 h / -20 °C

With 1H-tetrazole; hydrogenchloride; dmap; sodium cyanoborohydride; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Cyclization / 3: Esterification / 4: Ring cleavage / 5: phosphitylation / 6: Oxidation;

DOI:10.1246/bcsj.70.1435

Reference yield:

allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside (188583-14-4) → allyl 6-O-benzyl-3-O-[(R)-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 (192196-07-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 12.3 g / (+)-camphor-10-sulfonic acid / tetrahydrofuran / 3 h / Heating

2: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

3: 74 percent / sodium cyanotrihydroborate; hydrogen chloride / tetrahydrofuran / 1 h / 25 °C

4: 1H-tetrazole / CH₂Cl₂ / 0.33 h / 20 °C

5: 894 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.08 h / -20 °C

With 1H-tetrazole; hydrogenchloride; dmap; sodium cyanoborohydride; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Esterification / 3: Ring cleavage / 4: phosphitylation / 5: Oxidation;

DOI:10.1246/bcsj.70.1435

upstream raw materials:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside

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

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

Downstream raw materials:

6-O-benzyl-3-O-[(R)-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