1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOFURANOSE 3,4,6-TRIACETATE

Base Information

• Chemical Name: 1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOFURANOSE 3,4,6-TRIACETATE
• CAS No.: 76512-89-5
• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.334
• Mol file: 76512-89-5.mol

Synonyms:1,3,6-Trioxaspiro[4.4]nonane,b-D-fructofuranose deriv.

Chemical Property of 1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOFURANOSE 3,4,6-TRIACETATE

Chemical Property:

• PSA: 106.59000
• LogP: 0.29090

Purity/Quality:

96% ^*data from raw suppliers

3,4,6-Tri-O-acetyl-1,2-O-isopropylidene-b-D-fructofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOFURANOSE 3,4,6-TRIACETATE

There total 3 articles about 1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOFURANOSE 3,4,6-TRIACETATE 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:

2,2-dimethoxy-propane (77-76-9) → 3,4,6-tri-O-acetyl-1,2-O-isopropylidene-β-D-fructofuranose (76512-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tin(II) chloride / 1,2-dimethoxy-ethane / 0.5 h / Heating

2: pyridine

With pyridine; tin(ll) chloride; In 1,2-dimethoxyethane;

DOI:10.1039/c39800000882

Reference yield:

acetic anhydride (108-24-7) + 1,2-O-Isopropylidene-β-D-fructofuranose (76549-76-3) → 3,4,6-tri-O-acetyl-1,2-O-isopropylidene-β-D-fructofuranose (76512-89-5)

Guidance literature:

With pyridine; Yield given;

DOI:10.1039/c39800000882

Reference yield:

D-fructose (470-23-5,470-24-6,10247-46-8,10489-79-9,35673-97-3,36441-90-4,36441-92-6,36468-68-5,37500-17-7,40461-86-7,40461-87-8,41579-20-8,41846-98-4,41846-99-5,41847-00-1,41847-01-2,41847-02-3,41847-03-4,41847-04-5,41847-05-6,41847-06-7,41847-51-2,41847-52-3,42744-42-3) + acetic anhydride (108-24-7) + 2,2-dimethoxy-propane (77-76-9) → 3-O-acetyl-1,2;4,5-di-O-isopropylidene-β-D-fructofuranose (26388-67-0) + 3,4,6-tri-O-acetyl-1,2-O-isopropylidene-β-D-fructofuranose (76512-89-5) + 3,4,5-tri-O-acetyl-1,2-O-isopropylidene-β-D-fructopyranose (26388-66-9)

Guidance literature:

With pyridine; tin(ll) chloride; Yield given. Multistep reaction. Yields of byproduct given; 1) dimethoxyethane, reflux, 25 min.; 2) 12 h;

DOI:10.1016/0008-6215(87)84006-5

upstream raw materials:

acetic anhydride

1,2-O-Isopropylidene-β-D-fructofuranose

D-fructose

2,2-dimethoxy-propane

Downstream raw materials:

6-O-benzoyl-1,2-O-isopropylidene-β-D-fructofuranose

Refernces

• 1、 Drijver, Laetitia Den,Holzapfel, Cedric W.,Dyk, Martha S. van,Kruger, Gert J.. "PHOTOCHEMICAL OXIDATION OF PARTIALLY PROTECTED DERIVATIVES OF α-D-GLUCOFURANOSE AND β-D-FRUCTOFURANOSE". . p. 65 - 74. Retrieved 2007/10/02.