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

Base Information

• Chemical Name: 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
• CAS No.: 143706-47-2
• Molecular Formula: C₅₆H₆₃Br₂ClO₁₃
• Molecular Weight: 1139.37

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 96.0%

4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside (143706-45-0) + Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (143706-44-9) → 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 (143706-47-2)

Guidance literature:

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane;

DOI:10.1021/ja00047a080

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → 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 (143706-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1: SnCl₄ / CH₂Cl₂

2: NaOMe / methanol / 2 h

3: Br₂, Et₄NBr / CH₂Cl₂

4: 50 percent / pyridine

5: NIS, Et₃SiOTf / CH₂Cl₂ / 0.05 h

With pyridine; N-iodo-succinimide; tetraethylammonium bromide; bromine; triethylsilyl trifluoromethyl sulfonate; 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) → 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 (143706-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1: SnCl₄ / CH₂Cl₂

2: NaOMe / methanol / 2 h

3: Br₂, Et₄NBr / CH₂Cl₂

4: 50 percent / pyridine

5: NIS, Et₃SiOTf / CH₂Cl₂ / 0.05 h

With pyridine; N-iodo-succinimide; tetraethylammonium bromide; bromine; triethylsilyl trifluoromethyl sulfonate; sodium methylate; tin(IV) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00095a020

upstream raw materials:

4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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

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->3)-2,4-di-O-benzyl-α-D-mannopyranoside

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