Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-acetate

Base Information

• Chemical Name: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-acetate
• CAS No.: 159734-71-1
• Molecular Formula: C36H33NO7S
• Molecular Weight: 623.727
• Mol file: 159734-71-1.mol

Synonyms:Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-acetate

Chemical Property of Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-acetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-acetate

There total 7 articles about Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside 4-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: 100.0%

acetic anhydride (108-24-7) + phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-71-1)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1080/07328309808002904

Reference yield:

phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / triethylsilane; trifluoroacetic anhydride; trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

2: 95 percent / pyridine / 16 h / 20 °C

With pyridine; triethylsilane; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1021/ja029346v

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-71-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / 15 h / Ambient temperature

2: NaOMe / methanol; CH₂Cl₂ / 2 h / Ambient temperature

3: TsOH*H₂O / acetonitrile / 15 h / Ambient temperature

4: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, rt, overnight

5: 100 percent / 4 Angstroem MS, NaBH₃CN / tetrahydrofuran / Ambient temperature

6: 100 percent / pyridine / Ambient temperature

With pyridine; 4 Angstroem MS; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1080/07328309808002904

upstream raw materials:

acetic anhydride

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

phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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

Downstream raw materials:

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

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

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

methyl 2,3-di-O-benzoyl-4,6-O-((R)-1-methoxycarbonylethylidene)-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3) 2,4-di-O-benzyl-β-L-fucopyranoside