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

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 196697-91-3
• Molecular Formula: C₄₁H₃₇NO₆S
• Molecular Weight: 671.814
• Mol file: 196697-91-3.mol

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

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

There total 6 articles about phenyl 3,4,6-tri-O-benzyl-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: 72.0%

benzyl bromide (100-39-0) + 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 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (196697-91-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo050185y

Reference yield:

phthalic anhydride (85-44-9) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (196697-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃

2: pyridine

3: BF₃*Et₂O

4: aq. HCl

5: NaH / dimethylformamide

With pyridine; hydrogenchloride; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; In N,N-dimethyl-formamide;

DOI:10.1039/b504558d

Reference yield:

2-deoxy-2-phthalimido-D-glucopyranose (31505-45-0) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (196697-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: BF₃*Et₂O

3: aq. HCl

4: NaH / dimethylformamide

With pyridine; hydrogenchloride; boron trifluoride diethyl etherate; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/b504558d

upstream raw materials:

benzyl bromide

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

phthalic anhydride

2-deoxy-2-phthalimido-D-glucopyranose

Downstream raw materials:

2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione