Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 852568-17-3
• Molecular Formula: C₄₈H₄₉ClN₄O₁₄
• Molecular Weight: 941.388

Synonyms:

Chemical Property of Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 3 articles about Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl 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:

4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (852568-11-7) + 5-azido-1-pentanol (170220-11-8) → Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (852568-17-3)

Guidance literature:

4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside; 5-azido-1-pentanol; With N-iodo-succinimide; 4 A molecular sieve; In dichloromethane; acetonitrile; at 0 ℃; for 1h;

With trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; acetonitrile; at 5 ℃; for 1h;

DOI:10.1055/s-2005-863751

Reference yield:

2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl bromide → Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (852568-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / -40 °C

2.1: 4 Angstroem molecular sieves; NIS / CH₂Cl₂; acetonitrile / 1 h / 0 °C

2.2: 4 Angstroem molecular sieves; TfOH / CH₂Cl₂; acetonitrile / 1 h / 5 °C

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1055/s-2005-863751

Reference yield:

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside (141342-83-8) → Benzoic acid (2S,4aR,6S,7R,8S,8aS)-6-[(2R,3S,4R,5R,6R)-6-(5-azido-pentyloxy)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(2-chloro-acetoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (852568-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / -40 °C

2.1: 4 Angstroem molecular sieves; NIS / CH₂Cl₂; acetonitrile / 1 h / 0 °C

2.2: 4 Angstroem molecular sieves; TfOH / CH₂Cl₂; acetonitrile / 1 h / 5 °C

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1055/s-2005-863751

upstream raw materials:

4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

5-azido-1-pentanol

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside

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