isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose

Base Information

• Chemical Name: isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose
• CAS No.: 158818-97-4
• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.596
• Mol file: 158818-97-4.mol

Synonyms:isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose

Chemical Property of isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose

There total 9 articles about isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose 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: 91.0%

isopropyl alcohol (67-63-0,8013-70-5) + 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranose-2-ulosyl bromide (158818-92-9) → isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose (158818-97-4)

Guidance literature:

With 3 A molecular sieve; silver carbonate; In dichloromethane; for 0.00833333h; Ambient temperature;

DOI:10.1021/jo00101a035

Reference yield:

iso-propyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (170428-28-1) → isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose (158818-97-4)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; at 20 ℃;

DOI:10.1016/j.tetasy.2004.06.019

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4) → isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose (158818-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / 33percent HBr / acetic acid; CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) NaI, 2.) DBU / 1.) acetone, r.t., 15 min, 2.) 45 min

3: 92 percent / NBS, molecular sieves (3 Angstroem) / ethanol; CH₂Cl₂ / 0.03 h / 25 °C

4: 91 percent / Ag₂CO₃, molecular sieves (3 Angstroem) / CH₂Cl₂ / 0.01 h / Ambient temperature

With N-Bromosuccinimide; 3 A molecular sieve; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; sodium iodide; In ethanol; dichloromethane; acetic acid;

DOI:10.1021/jo00101a035

upstream raw materials:

isopropyl alcohol

3,4,6-tri-O-benzyl-α-D-arabino-hexopyranose-2-ulosyl bromide

iso-propyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

C₃₀H₃₅NO₆

C₃₀H₃₅NO₆

isopropyl 3,4,6-tri-O-benzyl-2-benzoyloxyimino-2-deoxy-β-D-arabino-hexopyranoside

isopropyl 3,4,6-tri-O-benzyl-2-benzoyloxyimino-2-deoxy-β-D-arabino-hexopyranoside