1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose

Base Information

• Chemical Name: 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose
• CAS No.: 2774-28-9
• Molecular Formula: C12H18O5
• Molecular Weight: 242.272
• Hs Code.: 2940000080
• Mol file: 2774-28-9.mol

Synonyms:1-O,2-O:5-O,6-O-Bis(1-methylethylidene)-3-deoxy-α-D-erythro-3-hexenofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-hexa-3-enofuranose

Chemical Property of 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose

Chemical Property:

• PSA: 46.15000
• LogP: 1.52960
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform; Methanol

Purity/Quality:

3-Deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3,4-enofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3,4-enofuranose is an intermediate in synthesizing 6R,7R,8aR-Glucosepane (G595300), one of the eight diastereomers of glucosepane. Glucosepane is a structurally complex protein posttranslational modification that is believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging.

Technology Process of 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose

There total 56 articles about 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose 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: 98.0%

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose (55951-93-4) → 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(03)01098-0

Reference yield: 94.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2006.03.116

Reference yield: 84.0%

1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside (3253-75-6) → 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1039/c39920000759

upstream raw materials:

1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose

tetramethyl ammonium acetate

2,2,2-Trifluoro-1,1-diphenyl-ethanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Downstream raw materials:

isolevoglucosenone

(3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Refernces

• 1、 Huo, Shiyong,Li, Yueqing,Liang, Chaoyan,Liu, Jihong,Zhao, Weijie. "Synthesis of novel N-carbohydrate-derived heterocyclic compounds by nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates". . p. 75 - 84. Retrieved 2011.
• 2、 Hussain, Nazar,Babu Tatina, Madhu,Mukherjee, Debaraj. "Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene". . p. 2666 - 2677. Retrieved 2018.
• 3、 Horton, Derek,Roski, James P.,Norris, Peter. "Cycloaddition of cyclopentadiene to 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose. Synthesis and representative chemistry of 1,6-anhydro-2,3-dideoxy-β-D-glycero-hex-2-enopyran-4-ulose ("isolevoglucosenone")". . p. 3783 - 3793. Retrieved 1996.
• 4、 Nagy, Adrienn,Csordás, Barbara,Zsoldos-Mády, Virág,Pintér, István,Farkas, Viktor,Perczel, András. "C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies". . p. 223 - 240. Retrieved 2017/02/05.