1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE

Base Information

• Chemical Name: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE
• CAS No.: 25018-67-1
• Molecular Formula: C12H20O6
• Molecular Weight: 260.287
• Hs Code.: 2940000080
• Mol file: 25018-67-1.mol

Synonyms:Spiro[1,3-dioxolane-4,6'-[6H-1,3]dioxolo[4,5-c]pyran], b-D-fructopyranose deriv.;1,2:4,5-Di-O-isopropylidene-b-D-fructopyranose;Fructopyranose,1,2:4,5-di-O-isopropylidene-, b-D- (8CI);1,2:4,5-Di-O-isopropylidene-b-fructopyranose;(3a'R,4S,7'S,7a'S)-2,2,2',2'-Tetramethyltetrahydrospiro[1,3-dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'-ol (non-preferred name);

Chemical Property of 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE

Chemical Property:

• Melting Point: 116-117 °C
• Boiling Point: 379.03 °C at 760 mmHg
• PKA: 13.88±0.60(Predicted)
• Flash Point: 183.031 °C
• PSA: 66.38000
• Density: 1.287 g/cm³
• LogP: 0.37680
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

1,2,4,5-Di-O-isopropylidene-b-D-fructopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2:4,5-bis-O-(1-Methylethylidene)-β-D-Fructopyranose is a reagent in the synthesis of antibacterial/antifungal monosaccaride esters. Also used in the synthesis of antihyperlipidemic novel compounds involving glycosyl fructose derivatives.

Technology Process of 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE

There total 15 articles about 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE 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: 67.8%

D-fructose (7660-25-5) + acetone (67-64-1) → 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose (15080-25-8,18422-54-3,18604-28-9,20880-93-7,25018-67-1,83602-34-0)

Guidance literature:

With sulfuric acid; sodium hydroxide; at 0 - 50 ℃; Further stages;

DOI:10.1002/mabi.201600529

Reference yield: 47.0%

L-fructose (57-48-7,87-79-6,87-81-0,551-68-8,3615-39-2,3615-56-3,6035-50-3,7776-48-9,16354-64-6,17598-81-1,17598-82-2,23140-52-5,30237-26-4,65732-90-3,73952-10-0,73952-11-1,139686-85-4,18875-34-8) → 1,2:4,5-di-O-isopropylidene-β-L-fructopyranose (15080-25-8,18422-54-3,18604-28-9,20880-93-7,25018-67-1,83602-34-0)

Guidance literature:

With sulfuric acid; In acetone; for 3h;

DOI:10.1016/S0008-6215(00)80782-X

Reference yield: 45.0%

D-Fructose (57-48-7,18875-34-8) + acetone (67-64-1) → 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (20880-92-6) + 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose (25018-67-1)

Guidance literature:

Yields of byproduct given;

upstream raw materials:

D-Fructose

acetone

Sucrose

D-raffinose

Downstream raw materials:

O¹,O²;O⁴,O⁵-diisopropylidene-O³-(toluene-4-sulfonyl)-β-D-fructopyranose

O³-diphenoxyphosphoryl-O¹,O²;O⁴,O⁵-diisopropylidene-β-D-fructopyranose

D-arabino-1,4,5,6-Tetrahydroxy-3-phosphonooxy-hexan-2-on

3-O-Benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose

Refernces

• 1、 Zhou, Xu,Qin, Xianyan,Gong, Tao,Zhang, Zhi-Rong,Fu, Yao. "d-Fructose Modification Enhanced Internalization of Mixed Micelles in Breast Cancer Cells via GLUT5 Transporters". . . Retrieved 2017/07/18.
• 2、 Ager, David J.,Anderson, Ken,Oblinger, Eric,Shi, Yian,Vanderroest, James. "An epoxidation approach to a chiral lactone: Application of the Shi epoxidation". . p. 44 - 51. Retrieved 2012/12/26.