Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Base Information

• Chemical Name: Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside
• CAS No.: 143706-44-9
• Molecular Formula: C₂₇H₃₃Br₂ClO₇
• Molecular Weight: 664.816

Synonyms:Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Chemical Property of Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

There total 5 articles about Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside 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: 50.0%

(2S,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-(4,5-dibromo-pentyloxy)-6-hydroxymethyl-tetrahydro-pyran-4-ol (1054617-13-8) + Chloroacetic anhydride (541-88-8) → Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (143706-44-9)

Guidance literature:

With pyridine;

DOI:10.1021/jo00095a020

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (143706-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: SnCl₄ / CH₂Cl₂

2: NaOMe / methanol / 2 h

3: Br₂, Et₄NBr / CH₂Cl₂

4: 50 percent / pyridine

With pyridine; tetraethylammonium bromide; bromine; sodium methylate; tin(IV) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00095a020

Reference yield:

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose (80738-50-7) → Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (143706-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: SnCl₄ / CH₂Cl₂

2: NaOMe / methanol / 2 h

3: Br₂, Et₄NBr / CH₂Cl₂

4: 50 percent / pyridine

With pyridine; tetraethylammonium bromide; bromine; sodium methylate; tin(IV) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00095a020

upstream raw materials:

(2S,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-(4,5-dibromo-pentyloxy)-6-hydroxymethyl-tetrahydro-pyran-4-ol

Chloroacetic anhydride

n-Pent-4-enyl alcohol

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose

Downstream raw materials:

Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<(3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)>-6-O-(chloroacetyl)-2,4-di-O-benzyl-α-D-mannopyranoside

Chloro-acetic acid (2R,3R,4S,5S,6S)-4-((2R,3S,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5-bis-benzyloxy-6-(4,5-dibromo-pentyloxy)-tetrahydro-pyran-2-ylmethyl ester

Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-mannopyranoside

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