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

Base Information

• Chemical Name: phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 208644-70-6
• Molecular Formula: C₃₄H₂₉NO₆S
• Molecular Weight: 579.673
• Mol file: 208644-70-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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: 95.0%

benzyl bromide (100-39-0) + phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6)

Guidance literature:

With 15-crown-5; sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 19h; Reagent/catalyst; Inert atmosphere;

Reference yield:

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / Et₃N / acetonitrile / 20 °C

2: 90 percent / Bu₄NI; NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo050185y

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6)

Guidance literature:

Multi-step reaction with 4 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

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1080/07328309808002904

upstream raw materials:

benzyl bromide

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

benzaldehyde dimethyl acetal

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Downstream raw materials:

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

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

methyl 4-O-acetyl-2-azido-3-O-{2-azido-3-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide