3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose
• CAS No.: 125946-77-2
• Molecular Formula: C₃₅H₃₃NO₇
• Molecular Weight: 579.65
• Mol file: 125946-77-2.mol

Synonyms:3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose

Chemical Property of 3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose

There total 12 articles about 3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose 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: 99.0%

phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (196697-91-3) → 2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (125946-77-2)

Guidance literature:

With N-Bromosuccinimide; In water; acetone; at -15 ℃; for 1h;

DOI:10.1021/jo050185y

Reference yield: 82.0%

allyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (125946-76-1) → 2-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (125946-77-2)

Guidance literature:

With sodium acetate; acetic acid; palladium dichloride; at 20 ℃; for 20h;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

benzyl bromide (100-39-0) → 3,4,6-tri-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose (125946-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaH / 1) THF, 15 min, 2) THF, 36 h, r. t.

2: Rh(PPh₃)3Cl / ethanol; H₂O / 18 h / Heating

3: HgO(yellow), HgCl₂ / acetone; H₂O / 18 h

With sodium hydride; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In ethanol; water; acetone;

DOI:10.1016/0008-6215(91)80123-5

upstream raw materials:

allyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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

benzyl bromide

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

Downstream raw materials:

3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside