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

Base Information

• Chemical Name: 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
• CAS No.: 177421-15-7
• Molecular Formula: C₄₉H₅₁NO₁₂
• Molecular Weight: 845.943

Synonyms: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

Chemical Property of 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

Chemical Property:

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Useful:

Technology Process of 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

There total 5 articles about 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 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: 99.6%

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)-2-(2-chloro-acetoxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester (177421-14-6) → 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)

Guidance literature:

With 2,6-dimethylpyridine; thiourea; In methanol; dichloromethane; for 36h; Ambient temperature;

DOI:10.1080/07328309608005652

Reference yield:

phenyl 3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-53-3) → 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)

Guidance literature:

Multi-step reaction with 3 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

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) → 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)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1080/07328309608005652

upstream raw materials:

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)-2-(2-chloro-acetoxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

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

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

methyl 3-O-allyl-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-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-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

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

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