Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside
• CAS No.: 97242-79-0
• Molecular Formula: C29H29 N O7
• Molecular Weight: 503.552
• DSSTox Substance ID: DTXSID50469885
• Nikkaji Number: J2.356.139E
• Wikidata: Q82297809
• Mol file: 97242-79-0.mol

Synonyms:97242-79-0;Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside;Methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranoside;2-[(2R,3R,4R,5S,6R)-5-hydroxy-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione;DTXSID50469885;AKOS030254631;W-204150;Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido- beta -D-glucopyranoside;Methyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-beta-D-glucopyranoside

Chemical Property of Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside

Chemical Property:

• PSA: 94.53000
• LogP: 3.08100
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 503.19440226
• Heavy Atom Count: 37
• Complexity: 741

Purity/Quality:

95% ^*data from raw suppliers

Methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)N4C(=O)C5=CC=CC=C5C4=O
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)N4C(=O)C5=CC=CC=C5C4=O
• Uses: Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (cas# 97242-79-0) is a compound useful in organic synthesis.

Technology Process of Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside

There total 20 articles about Methyl 3,6-Di-O-benzyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoside 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: 95.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (81927-58-4) → methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0)

Guidance literature:

With hydrogenchloride; molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 1h; Ambient temperature;

DOI:10.1139/v85-182

Reference yield: 70.0%

methanol (67-56-1) + ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1039/c2ob07066a

Reference yield: 70.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (97276-96-5) → methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 5h; Ambient temperature;

DOI:10.1016/0008-6215(90)84225-J

upstream raw materials:

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

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

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

methyl trifluoromethanesulfonate

Downstream raw materials:

methyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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

methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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