1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE

Base Information

• Chemical Name: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE
• CAS No.: 10578-85-5
• Molecular Formula: C12H20 O7
• Molecular Weight: 276.287
• Mol file: 10578-85-5.mol

Synonyms:D-ribo-Hexofuranos-3-ulose,1,2:5,6-di-O-isopropylidene-, hydrate, a- (8CI); Furo[2,3-d]-1,3-dioxole, a-D-ribo-hexofuranos-3-ulosederiv.

Chemical Property of 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE

Chemical Property:

• Melting Point: 107-108 °C
• Boiling Point: 434.2±45.0 °C(Predicted)
• PKA: 11.11±0.60(Predicted)
• PSA: 95.84000
• Density: 1.317±0.06 g/cm3(Predicted)
• LogP: -0.36910

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2:5,6-Di-O-isopropylidene-a-D-ribo-hexofuranose-3-ulose monohydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE

There total 10 articles about 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE 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: 100.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate (10578-85-5)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; sodium acetate; sodium bromide; In ethyl acetate; at 3 - 7 ℃; for 8.5h; pH=11.5 - 12.5; pH-value; Temperature; Time; Large scale;

Reference yield: 90.0%

cyclohexa-1,3-diene (1165952-91-9) + 3-chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitroso-α-D-glucofuranose (266306-47-2) → 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate (10578-85-5) + (1S,4R)-3-aza-2-oxabicyclo<2,2,2>oct-5-ene hydrochloride (266306-44-9)

Guidance literature:

In chloroform; water; isopropyl alcohol; at 0 ℃; for 3h;

Reference yield: 80.0%

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) + O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate (180627-08-1) → 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate (10578-85-5) + [(diethoxy-thiophosphoryl)-difluoro-methyl]-phosphonothioic acid O,O-diethyl ester + 3-(O,O-diethylphosphonothio)difluoromethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (482621-37-4)

Guidance literature:

O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate; With tert.-butyl lithium; at -78 ℃;

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose; at -78 - 0 ℃;

DOI:10.1021/ja027850u

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

cyclohexa-1,3-diene

3-chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitroso-α-D-glucofuranose

Downstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose benzoylhydrazone

6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose

Acetic acid (3aR,5S,6R,6aR)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-O-acetyl-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose

Refernces

• 1、 Blandino, Maureen,McNelis, Edward. "Rearrangements of haloalkynol derivatives of glucofuranose". . p. 3387 - 3390. Retrieved 2002.
• 2、 -. "LARGE SCALE PROCESS FOR PREPARING 1,2,4, 6-TETRA-0-ACETYL-3-AZID0-3-DE0XY-D-GALACT0PYRAN0SIDE". Page/Page column 9; 10. . Retrieved 2021/10/11.
• 3、 Lopin, Chrystel,Gautier, Arnaud,Gouhier, Geraldine,Piettre, Serge R.. "First and efficient synthesis of phosphonodifluoromethylene analogues of nucleoside 3′-phosphates: Crucial role played by sulfur in construction of the target molecules". . p. 14668 - 14675. Retrieved 2007/10/03.