phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 213185-36-5
• Molecular Formula: C₄₂H₄₂ClN₃O₁₁S
• Molecular Weight: 832.328

Synonyms:phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 8 articles about phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 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:

Chloroacetic anhydride (541-88-8) + Benzoic acid (2S,3R,4R,5S,6S)-4-[(4aR,6R,7R,8R,8aS)-7-azido-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester → phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (213185-36-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1021/jo980660a

Reference yield:

benzyl bromide (100-39-0) → phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (213185-36-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

5.1: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

7.1: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation / 5.1: Deacetylation / 6.1: Cyclization / 7.1: Acylation;

DOI:10.1021/jo980660a

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → phenyl [2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (213185-36-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

5.1: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

7.1: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation / 5.1: Deacetylation / 6.1: Cyclization / 7.1: Acylation;

DOI:10.1021/jo980660a

upstream raw materials:

Chloroacetic anhydride

benzyl bromide

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-α-D-galactopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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