2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione

Base Information

• Chemical Name: 2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione
• CAS No.: 129575-89-9
• Molecular Formula: C35H33 N O8
• Molecular Weight: 595.649
• DSSTox Substance ID: DTXSID60451534
• Nikkaji Number: J971.996B
• Wikidata: Q82271602
• Mol file: 129575-89-9.mol

Synonyms:129575-89-9;4-Methoxyphenyl 3,6-Di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside;2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione;2-[(2S,3R,4R,5S,6R)-5-hydroxy-2-(4-methoxyphenoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione;SCHEMBL3625228;DTXSID60451534;QKFDXGIKVGVBGT-PVEIOGNQSA-N;MFCD08276391;AS-74994;M1615;T71691;J-005693;4-Methoxyphenyl 2-phthalimidyl-3-O,6-O-dibenzyl-2-deoxy-beta-D-glucopyranoside;4-methoxyphenyl-3,6-di-o-benzyl-2-deoxy-2-phthalimido-beta-d-glucopyranoside;2-[(2S,3R,4R,5S,6R)-4-(benzyloxy)-6-[(benzyloxy)methyl]-5-hydroxy-2-(4-methoxyphenoxy)oxan-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione;beta-D-Glucopyranoside, 4-methoxyphenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-

Chemical Property of 2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione

Chemical Property:

• Vapor Pressure: 4.79E-24mmHg at 25°C
• Refractive Index: 1.66
• Boiling Point: 756.4°C at 760 mmHg
• PKA: 12.82±0.70(Predicted)
• Flash Point: 411.3°C
• PSA: 103.76000
• Density: 1.35g/cm³
• LogP: 4.56470
• Storage Temp.: Freezer
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 595.22061701
• Heavy Atom Count: 44
• Complexity: 904

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Methoxyphenyl 3,6-Di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C(C(O2)COCC3=CC=CC=C3)O)OCC4=CC=CC=C4)N5C(=O)C6=CC=CC=C6C5=O
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COCC3=CC=CC=C3)O)OCC4=CC=CC=C4)N5C(=O)C6=CC=CC=C6C5=O
• Uses: 4-Methoxyphenyl 3,6-Di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (CAS# 129575-89-9) is a useful glycoside building block used in the synthesis of glycans.

Technology Process of 2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-1,3-dione

There total 15 articles about 2-((2S,3R,4R,5S,6R)-4-(Benzyloxy)-6-((benzyloxy)methyl)-5-hydroxy-2-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)isoindoline-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: 86.0%

p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-88-8) → p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-89-9)

Guidance literature:

p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside; With triethylsilane; In dichloromethane; at 0 ℃; for 0.166667h;

With trifluoroacetic acid; In dichloromethane; for 0.5h;

DOI:10.1039/c8ob01046c

Reference yield: 80.0%

benzyl bromide (100-39-0) + p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (179739-15-2) → p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-89-9)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In acetonitrile; for 72h; Heating;

DOI:10.1080/00397919608005219

Reference yield: 60.0%

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-42-0) + benzyl bromide (100-39-0) → p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-89-9) + p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (179739-15-2)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In acetonitrile; for 144h; Heating;

DOI:10.1080/00397919608005219

upstream raw materials:

p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl bromide

para-MethoxyPhenyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

p-methoxyphenyl 3,6-di-O-benzyl-4-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

C₇₂H₇₉NO₁₄SSi

phenyl 2-O-(2-iodo-1-(p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosid-4-O-yl)propyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

4-methoxyphenyl O-(3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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