3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose
• CAS No.: 72858-55-0
• Molecular Formula: C20H21NO10
• Molecular Weight: 435.387
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID40448629
• Nikkaji Number: J1.124.178F
• Mol file: 72858-55-0.mol

Synonyms:72858-55-0;3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose;(2R,3S,4R,5R)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate;[(2R,3S,4R,5R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-hydroxyoxan-2-yl]methyl acetate;3,4,6-Tri-o-acetyl-2-deoxy-2-(phthalimido)-d-glucopyranose;SCHEMBL4178413;DTXSID40448629;VHMUDSSZBIYPEM-UFMXMSTQSA-N;s11368;CS-0457559;A914702;2-Phthalimidyl-2-deoxy-D-glucopyranose 3,4,6-triacetate;(2R,3S,4R,5R)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-hydroxytetrahydro-2H-pyran-3,4-diyldiacetate

Chemical Property of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Chemical Property:

• Melting Point: 157-158 °C(Solv: methanol (67-56-1))
• Boiling Point: 569.9±50.0 °C(Predicted)
• PKA: 11.62±0.70(Predicted)
• PSA: 145.74000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: -0.26720
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 435.11654587
• Heavy Atom Count: 31
• Complexity: 743

Purity/Quality:

97% ^*data from raw suppliers

3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)O)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(O1)O)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C

Technology Process of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

There total 4 articles about 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 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: 22.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) + benzyl 2-acetamido-6-O-benzyl-3-O-[(R)-1-(methoxycarbonyl)ethyl]-2-deoxy-α-d-glucopyranoside (107671-54-5) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) + benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (112289-92-6) + 3,4,6,3',4',6'-hexa-O-acetyl-2,2'-dideoxy-2,2'-diphthalimido-β,β-trehalose (112302-57-5)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/0008-6215(87)80218-5

Reference yield:

phthalic anhydride (85-44-9) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 0.25 h / 20 °C

1.2: 1 h

1.3: 0.67 h / 20 - 45 °C

2.1: pyridine; dmap / dichloromethane / 2 h / 20 °C

3.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium methylate; hydrazinium monoacetate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2012.06.027

Reference yield:

phthalic anhydride (85-44-9) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (72858-55-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydrogencarbonate; sodium hydroxide / methanol; water; acetone / 0 - 21 °C

2: pyridine / 16 h / 21 °C

3: acetic acid; ethylenediamine / tetrahydrofuran / 16 h / 21 °C / Inert atmosphere

With pyridine; sodium hydrogencarbonate; acetic acid; ethylenediamine; sodium hydroxide; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1021/ol2013704

upstream raw materials:

phthalic anhydride

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

benzyl 2-acetamido-6-O-benzyl-3-O-[(R)-1-(methoxycarbonyl)ethyl]-2-deoxy-α-d-glucopyranoside

Downstream raw materials:

4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate

cholesteryl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

C₃₃H₃₃NO₁₁