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

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-, 3-acetate
• CAS No.: 125520-04-9
• Molecular Formula: C₂₅H₂₅NO₇S
• Molecular Weight: 483.542
• DSSTox Substance ID: DTXSID201104011
• Mol file: 125520-04-9.mol

Synonyms:125520-04-9;beta-D-Glucopyranoside, ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-[(R)-phenylmethylene]-1-thio-, 3-acetate;DTXSID201104011

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-, 3-acetate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 483.13517331
• Heavy Atom Count: 34
• Complexity: 763

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCSC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)OC(=O)C)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)OC(=O)C)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-, 3-acetate

There total 5 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-, 3-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: 88.0%

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) + acetic anhydride (108-24-7) → ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (125520-04-9)

Guidance literature:

With pyridine; for 18h;

DOI:10.1021/jo00296a055

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) → ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (125520-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 4.83 h / 0 - 20 °C

1.2: 74 percent / EtSH; TMSOTf / CH₂Cl₂ / 1.5 h / 20 °C

2.1: NaOMe / methanol / 2 h / 20 °C

3.1: 3.71 g / p-TsOH*H₂O / dimethylformamide / 70 °C

4.1: DMAP / pyridine / 1 h / 20 °C

With dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600515

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (125520-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.71 g / p-TsOH*H₂O / dimethylformamide / 70 °C

2: DMAP / pyridine / 1 h / 20 °C

With dmap; toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600515

upstream raw materials:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

acetic anhydride

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

benzaldehyde dimethyl acetal

Downstream raw materials:

Methyl 2-O-(3-O-Acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside

4-(pyridin-2-yl)thiazole-2-yl 3-O-acetyl-2-deoxy-4,6-O-benzylidene-2-phthalimido-1-thio-β-D-glucopyranoside

4-methoxyphenyl (3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[4-O-benzyl-2-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside