[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate
• CAS No.: 76101-13-8
• Molecular Formula: C21H23 N O10
• Molecular Weight: 449.414
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID70550704
• Nikkaji Number: J710.730G
• Wikidata: Q72491747
• Mol file: 76101-13-8.mol

Synonyms:76101-13-8;[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate;METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE;(2R,3S,4R,5R,6R)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-3,4-diyl diacetate;DTXSID70550704;[(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate;Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside;Methyl 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-b-D-glucopyranoside;Methyl 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-beta-D-glucopyranoside;W-203741;Methyl 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-?-D-glucopyranoside;(2R,3S,4R,5R,6R)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-methoxytetrahydro-2H-pyran-3,4-diyldiacetate;Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-beta-D-glucopyranoside

Chemical Property of [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate

Chemical Property:

• Melting Point: 150-155oC
• Boiling Point: 553.8±50.0 °C(Predicted)
• PKA: -2.53±0.20(Predicted)
• PSA: 134.74000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 0.38690
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 449.13219593
• Heavy Atom Count: 32
• Complexity: 759

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3,4,6-tri-O-acetyl-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: CC(=O)OCC1C(C(C(C(O1)OC)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
• Uses: Methyl 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (cas# 76101-13-8) is a compound useful in organic synthesis.

Technology Process of [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate

There total 1 articles about [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methoxyoxan-2-yl]methyl acetate 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:

phthalic anhydride (85-44-9) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (76101-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: hydrogen chloride / Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin

With pyridine; hydrogenchloride;

Reference yield:

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (76101-13-8) → methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe / methanol / 3 h

2: p-TsOH / acetonitrile / 0.33 h

3: NaH / dimethylformamide / 20 °C

4: methyl orange; NaCNBH₃; HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; sodium methylate; methyl orange; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile; 1: Deacetylation / 2: Condensation / 3: Alkylation / 4: Reduction;

DOI:10.1021/jo991812k

Reference yield:

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (76101-13-8) → methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside (81927-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butoxide / methanol

2: p-TsOH / acetonitrile

With potassium tert-butylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

upstream raw materials:

phthalic anhydride

Downstream raw materials:

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

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

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

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

Refernces

• 1、 -. "SYNTHETIC SALT COMPLEXES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD". . . Retrieved 2015/10/05.