allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 157567-42-5
• Molecular Formula: C₂₆H₂₇NO₈
• Molecular Weight: 481.502
• Mol file: 157567-42-5.mol

Synonyms:allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-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: 90.0%

allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (202600-40-6) → allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (157567-42-5)

Guidance literature:

With aluminum (III) chloride; trimethylamine-borane; water; In tetrahydrofuran; at 20 ℃; Cooling with ice;

DOI:10.1016/j.carres.2016.11.015

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (120142-50-9) → allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (157567-42-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 18 h / Ambient temperature

2: 72 percent / BH₃*NMe₃, AlCl₃, 4 Angstroem molecular sieves / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<494::AID-CHEM494>3.0.CO;2-8

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (157567-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / HBr / acetic acid

2: 74 percent / Hg(CN)2

3: 53 percent / aq. HCl / acetone

4: 82 percent / TsOH

5: 91 percent / pyridine

6: 80 percent / NaBH₃CN, HCl

With pyridine; hydrogenchloride; hydrogen bromide; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; In acetic acid; acetone;

upstream raw materials:

allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl 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

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

Downstream raw materials:

C₅₅H₆₂N₂O₁₅Si

Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-4-yl ester