5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS No.: 2847-00-9
• Molecular Formula: C12H18O6
• Molecular Weight: 258.271
• Hs Code.: 29400090
• Mol file: 2847-00-9.mol

Synonyms:NSC 623655;5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol;EINECS 220-646-9;(3Ar,5R,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one;1,2:5,6-Bis-O-isopropylidene-alpha-D-ribo-hexofuranos-3-ulose

Chemical Property of 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property:

• Appearance/Colour: colorless very viscous liquid
• Vapor Pressure: 0.000152mmHg at 25°C
• Melting Point: 65-70°C
• Refractive Index: 1.471
• Boiling Point: 349.8 °C at 760 mmHg
• Flash Point: 165.4 °C
• PSA: 63.22000
• Density: 1.268 g/cm³
• LogP: 0.58340
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 258.11033829
• Heavy Atom Count: 18
• Complexity: 399

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2=C(C3C(O2)OC(O3)(C)C)O)C
• Uses: 1,2:5,6-Di-O-isopropylidene-α-D-ribo-hexofuranose-3-ulose _x000D_(mixture of keto and ketal forms) (cas# 2847-00-9) is a compound useful in organic synthesis.

Technology Process of 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol

There total 46 articles about 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ol 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%

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (4613-62-1) → 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 20 ℃;

DOI:10.17344/acsi.2016.2727

Reference yield: 100.0%

Cyclohepta-1,3-diene (876938-53-3) + 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-hexofuran-3-ulose (2847-00-9) + 8-oxa-9-azabicyclo<3.2.2>non-6-ene hydrochloride (95798-89-3)

Guidance literature:

In chloroform; water; isopropyl alcohol; at 4 ℃; for 48h;

Reference yield: 94.0%

1,2:5,6-di-O-isopropylidene-D-glucose → 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; for 1h; Heating;

DOI:10.1016/S0008-6215(00)90138-1

upstream raw materials:

acetic anhydride

1,2:5,6-di-O-isopropylidene-3-C-<(R,S)-nitro(methoxycarbonyl)methyl>-α-D-allofuranose

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

(1,2:5,6)-di-O-isopropylidene-D-gulose

Downstream raw materials:

2-[(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-1-(3-nitro-phenyl)-ethanone

1,2-isopropylidene-α-D-ribofuranose

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

2-[(2R,4S,5R)-2-Phenyl-4-((2S,4R,5S)-2-phenyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-5-trimethylsilanyloxy-[1,3]dioxan-5-yl]-thiazole

Refernces

• 1、 Baker et al.. "". . p. 299,307,309,315,316. Retrieved 1974.
• 2、 Ghannay, Siwar,Brahmi, Jihed,Aouadi, Ka?ss,Msadek, Moncef,Praly, Jean-Pierre. "Unprecedented 3-O-methyl-3-C-trifluoromethyl-d-ribono- (and l-lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d-hexose-derived cyclic ketones". . p. 111 - 114. Retrieved 2016.
• 3、 Sayyad, Ashik A.,Kaliappan, Krishna P.. "Sequential Enyne-Metathesis/Diels–Alder Strategy: Rapid Access to Sugar–Oxasteroid–Quinone Hybrids". . p. 5055 - 5065. Retrieved 2017.
• 4、 Liu, Xiao,Xia, Xueliang,Sun, Chenghai,Lin, Cai,Zhou, Yiqian,Hussain, Muzammal,Tang, Fei,Liu, Lu,Li, Xue,Zhang, Jiancun. "Synthesis and Evaluation of 2′-Deoxy-2′-Spirodiflurocyclopropyl Nucleoside Analogs". . p. 479 - 494. Retrieved 2016.
• 5、 Soler, Tatiana,Bachki, Abderrazak,Falvello, Larry R.,Foubelo, Francisco,Yus, Miguel. "Branched-chain functionalised carbohydrates via β-functionalised organolithium compounds". . p. 3939 - 3943. Retrieved 1998.
• 6、 Watanabe, Yoshihiko,Ono, Yojiro,Hayashi, Shigefumi,Ueno, Yoshio,Toru, Takeshi. "Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary". . p. 1879 - 1885. Retrieved 1996.
• 7、 Cote,Robyt. "Isolation and partial characterization of an extracellular glucansucrase from Leuconostoc mesenteroides NRRL B-1355 that synthesizes an alternating (1 goes to 6), (1 goes to 3)-alpha-D-glucan.". . p. 57 - 74. Retrieved 1982.
• 8、 Argentini, M.,Weinreich, R.,Oberti, Roberta,Ungaretti, Luciano. "SYNTHESIS AND CRYSTAL STRUCTURE OF 3-DEOXY-3-FLUORO-1,2:5,6-DI-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE". . p. 239 - 254. Retrieved 1986.
• 9、 Blade, Helen,Bradley, Derek,Diorazio, Louis,Evans, Timothy,Hayter, Barry R.,Howell, Gareth P.. "Modular Synthesis of Constrained Ethyl (cEt) Purine and Pyrimidine Nucleosides". . p. 5337 - 5343. Retrieved 2015.
• 10、 Candito, David A.,Ye, Yingchun,Quiroz, Ryan V.,Reutershan, Michael H.,Witter, David,Gadamsetty, Surendra B.,Li, Hongming,Saurí, Josep,Schneider, Sebastian E.,Lam, Yu-Hong,Palte, Rachel L.. "Development of a Flexible and Robust Synthesis of Tetrahydrofuro[3,4- b]furan Nucleoside Analogues". . p. 5142 - 5151. Retrieved 2021.