octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside

Base Information

• Chemical Name: octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside
• CAS No.: 224953-09-7
• Molecular Formula: C₈₃H₉₆O₁₆
• Molecular Weight: 1349.67

Synonyms:octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside

Chemical Property of octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside

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Technology Process of octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside

There total 7 articles about octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside 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: 87.0%

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (130525-72-3) + (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R)-3,4-bis-benzyloxy-5-octyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-3-ol (224953-06-4) → octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside (224953-09-7)

Guidance literature:

With 4 A molecular sieve; In dichloromethane; for 0.166667h;

With N-iodo-succinimide; In dichloromethane; for 0.333333h;

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside; (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R)-3,4-bis-benzyloxy-5-octyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-3-ol; With silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0040-4020(99)00260-4

Reference yield:

octanol (111-87-5) → octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside (224953-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 1.5 h / 20 °C

2.1: 0.5 g / sodium methoxide / methanol / 4 h / 20 °C

3.1: molecular sieves 4A / CH₂Cl₂ / 0.17 h

3.2: N-iodosuccinimide / CH₂Cl₂ / 0.33 h

3.3: 82 percent / silver triflate / CH₂Cl₂

4.1: 95 percent / sodium methoxide / methanol / 20 °C

5.1: molecular sieves 4A / CH₂Cl₂ / 0.17 h

5.2: N-iodosuccinimide / CH₂Cl₂ / 0.33 h

5.3: 87 percent / silver triflate / CH₂Cl₂

With 4 A molecular sieve; sodium methylate; In methanol; dichloromethane; 1.1: glycosylation / 2.1: Deacetylation / 3.1: glycosylation / 3.2: glycosylation / 3.3: glycosylation / 4.1: Deacetylation / 5.1: glycosylation / 5.2: glycosylation / 5.3: glycosylation;

DOI:10.1016/S0040-4020(99)00260-4

Reference yield:

5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride (121604-11-3) → octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside (224953-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 1.5 h / 20 °C

2.1: 0.5 g / sodium methoxide / methanol / 4 h / 20 °C

3.1: molecular sieves 4A / CH₂Cl₂ / 0.17 h

3.2: N-iodosuccinimide / CH₂Cl₂ / 0.33 h

3.3: 82 percent / silver triflate / CH₂Cl₂

4.1: 95 percent / sodium methoxide / methanol / 20 °C

5.1: molecular sieves 4A / CH₂Cl₂ / 0.17 h

5.2: N-iodosuccinimide / CH₂Cl₂ / 0.33 h

5.3: 87 percent / silver triflate / CH₂Cl₂

With 4 A molecular sieve; sodium methylate; In methanol; dichloromethane; 1.1: glycosylation / 2.1: Deacetylation / 3.1: glycosylation / 3.2: glycosylation / 3.3: glycosylation / 4.1: Deacetylation / 5.1: glycosylation / 5.2: glycosylation / 5.3: glycosylation;

DOI:10.1016/S0040-4020(99)00260-4

upstream raw materials:

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R)-3,4-bis-benzyloxy-5-octyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-3-ol

octanol

5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride

Downstream raw materials:

(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R)-3,4-bis-benzyloxy-5-octyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-ol

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