Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 177421-16-8
• Molecular Formula: C₅₁H₅₂ClNO₁₃
• Molecular Weight: 922.426

Synonyms:

Chemical Property of Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-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: 82.1%

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (177421-15-7) + Chloroacetic anhydride (541-88-8) → Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (177421-16-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1080/07328309608005652

Reference yield:

phenyl 3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-53-3) → Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (177421-16-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 88.3 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: 97 percent / NIS, molecular sieves 4 Angstroem, triflic acid / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 1 h

3: 99.6 percent / thiourea, 2,6-lutidine / methanol; CH₂Cl₂ / 36 h / Ambient temperature

4: 82.1 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; thiourea; In methanol; dichloromethane;

DOI:10.1080/07328309608005652

Reference yield:

methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (55697-53-5) → Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (177421-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NIS, molecular sieves 4 Angstroem, triflic acid / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 1 h

2: 99.6 percent / thiourea, 2,6-lutidine / methanol; CH₂Cl₂ / 36 h / Ambient temperature

3: 82.1 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; thiourea; In methanol; dichloromethane;

DOI:10.1080/07328309608005652

upstream raw materials:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chloroacetic anhydride

phenyl 3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

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