beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-

Base Information

• Chemical Name: beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-
• CAS No.: 99409-33-3
• Molecular Formula: C₂₃H₂₃NO₆S
• Molecular Weight: 441.505
• DSSTox Substance ID: DTXSID801108261
• Nikkaji Number: J3.027.975A
• Mol file: 99409-33-3.mol

Synonyms:99409-33-3;beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-;Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside;DTXSID801108261;Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio--D-glucopyranoside;Ethyl 4,6-O-benzylidene-2-deoxy-N-phthalimido-1- thio-beta-D-glucopyranoside;2-[(2R,4Ar,6S,7R,8R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione;Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-beta-D-glucopyranoside;ethyl 4,6-O-benzylidene-2-deoxy-N-(1,3-dioxo-2,3-dihydro- 1H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Chemical Property of beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-

Chemical Property:

• Boiling Point: 652.8±55.0 °C(Predicted)
• Density: 1.44±0.1 g/cm3(Predicted)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 441.12460863
• Heavy Atom Count: 31
• Complexity: 661

Purity/Quality:

98% by HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCSC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)N4C(=O)C5=CC=CC=C5C4=O
• Isomeric SMILES: CCS[C@H]1[C@@H]([C@H]([C@H]2[C@H](O1)CO[C@H](O2)C3=CC=CC=C3)O)N4C(=O)C5=CC=CC=C5C4=O

Technology Process of beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-

There total 8 articles about beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio- 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: 96.0%

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4) + benzaldehyde (100-52-7) → ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3)

Guidance literature:

With zinc(II) chloride; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200801035

Reference yield: 77.5%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4) → ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3)

Guidance literature:

With 3 A molecular sieve; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1081/CAR-120020480

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 2 h / 20 °C

2: 3.71 g / p-TsOH*H₂O / dimethylformamide / 70 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600515

upstream raw materials:

benzaldehyde dimethyl acetal

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6S,7R,8R,8aS)-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester