1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Base Information

• Chemical Name: 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside
• CAS No.: 1266609-51-1
• Molecular Formula: C₄₇H₅₃NO₁₅
• Molecular Weight: 871.936

Synonyms:1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Chemical Property of 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

There total 16 articles about 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside 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%

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) + diphenylphosphoryl-2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranoside (162111-85-5) → 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside (1266609-51-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside (1266609-51-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere

2.1: di(n-butyl)tin oxide / methanol / 1.5 h / Reflux; Inert atmosphere

2.2: 0.5 h / 100 °C / Inert atmosphere

3.1: sulfuric acid / 0.67 h / 20 °C / Inert atmosphere

4.1: hydrogen / 20 % Pd(OH)2/C / ethyl acetate / 760.05 Torr

5.1: dmap; pyridine / 2 h / 40 °C / Inert atmosphere

6.1: ammonia / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

7.1: benzylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

8.2: -78 °C / Inert atmosphere

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; benzylamine; 20 % Pd(OH)2/C; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → 1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside (1266609-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: di(n-butyl)tin oxide / methanol / 1.5 h / Reflux; Inert atmosphere

1.2: 0.5 h / 100 °C / Inert atmosphere

2.1: sulfuric acid / 0.67 h / 20 °C / Inert atmosphere

3.1: hydrogen / 20 % Pd(OH)2/C / ethyl acetate / 760.05 Torr

4.1: dmap; pyridine / 2 h / 40 °C / Inert atmosphere

5.1: ammonia / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

6.1: benzylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

7.2: -78 °C / Inert atmosphere

8.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; hydrogen; di(n-butyl)tin oxide; benzylamine; 20 % Pd(OH)2/C; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

upstream raw materials:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside

1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-4-(carbamoyloxy)-6-(((2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(acetoxymethyl)-2-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy)ethoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate

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