Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester

Base Information

• Chemical Name: Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester
• CAS No.: 754224-47-0
• Molecular Formula: C₅₉H₅₉N₃O₁₃
• Molecular Weight: 1018.13
• Mol file: 754224-47-0.mol

Synonyms:Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property of Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester

There total 10 articles about Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-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: 74.0%

methyl 4-azido-2,3-di-O-benzyl-6-O-(2-carboxybenzoyl)-4-deoxy-β-D-glucopyranoside (754224-51-6) + acetic acid (64-19-7,77671-22-8) + (1R,4S,5R,6S)-4,5,6-tri(benzyloxy)-1-C-(hydroxymethyl)cyclohex-2-en-1-ol (148347-74-4) → Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester (754224-47-0)

Guidance literature:

methyl 4-azido-2,3-di-O-benzyl-6-O-(2-carboxybenzoyl)-4-deoxy-β-D-glucopyranoside; (1R,4S,5R,6S)-4,5,6-tri(benzyloxy)-1-C-(hydroxymethyl)cyclohex-2-en-1-ol; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2h;

acetic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 5h;

DOI:10.1071/CH03185

Reference yield:

methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-D-glucopyranoside (754224-66-3) → Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester (754224-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / 4-(N,N-dimethylamino)pyridine; pyridine / 18 h / 20 °C

2.1: 1,3-dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h

2.2: 74 percent / 4-(N,N-dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h

With pyridine; dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1071/CH03185

Reference yield:

(1R,4S,5R,6S)-1-C-(acetoxymethyl)-4,5,6-tri(benzyloxy)cyclohex-2-en-1-ol (754224-71-0) → Phthalic acid 1-((1R,4S,5R,6S)-1-acetoxy-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl) ester 2-((2S,3R,4S,5R,6R)-3-azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester (754224-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 450 mg / Na; methanol / 1 h / 20 °C

2.1: 1,3-dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h

2.2: 74 percent / 4-(N,N-dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h

With methanol; dmap; sodium; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1071/CH03185

upstream raw materials:

methyl 4-azido-2,3-di-O-benzyl-6-O-(2-carboxybenzoyl)-4-deoxy-β-D-glucopyranoside

acetic acid

(1R,4S,5R,6S)-4,5,6-tri(benzyloxy)-1-C-(hydroxymethyl)cyclohex-2-en-1-ol

methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-D-glucopyranoside