1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol
• CAS No.: 13265-84-4
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• Hs Code.: 29339900
• European Community (EC) Number: 236-259-3
• Mol file: 13265-84-4.mol

Synonyms:1,2-dideoxy-D-arabino-hex-1-enopyranose;d-glucal

Chemical Property of 1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol

Chemical Property:

• Vapor Pressure: 1.77E-05mmHg at 25°C
• Melting Point: 62 °C
• Refractive Index: -10 ° (C=2, H2O)
• Boiling Point: 325.496 °C at 760 mmHg
• PKA: 12.79±0.60(Predicted)
• Flash Point: 150.655 °C
• PSA: 69.92000
• Density: 1.414 g/cm³
• LogP: -1.38700
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in Methanol.
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

D-Glucal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63-36/37/38
• Safety Statements: 22-24/25-53-36/37-26-25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=COC(C(C1O)O)CO
• Isomeric SMILES: C1=CO[C@@H](C([C@@H]1O)O)CO
• Uses: D-Glucal is an important building block for both solution- and solid-phase synthesis of oligosaccharides. It is an important building block for both solution- and solid-phase synthesis of oligosaccharides. Important building block for both solution- and solid-phase synthesis of oligosaccharides.

Technology Process of 1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol

There total 54 articles about 1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol 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%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → D-glucal (13265-84-4)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1021/jo00054a015

Reference yield: 95.0%

tri-O-acetyl-D-glucal → D-glucal (13265-84-4)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 5h;

DOI:10.1055/s-0032-1318113

Reference yield: 90.0%

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) → D-glucal (13265-84-4)

Guidance literature:

With sodium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; for 8h;

DOI:10.1016/S0040-4039(00)82294-7

upstream raw materials:

sodium methylate

D-glucal triacetate

3,4,6-tri-O-benzyl-D-glucal

6-O-tert-butyldimethylsilyl-D-glucal

Downstream raw materials:

6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

3,4,6-tri-O-benzyl-D-glucal

3,6-di-O-benzyl-D-glucal

1,5-Anhydro-4,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

Refernces

• 1、 Shafizadeh,Stacey. "-". . p. 3608. Retrieved 1952.
• 2、 Pathak. "A convenient method for O-deacetylation using IRA-400(OH) resin". . p. 83 - 85. Retrieved 1993.
• 3、 Borwitzky, Angela,Schareina, Thomas,Paetzold, Eckhard,Oehme, Guenther. "Syntheses of new bidentate thioethylphosphine ligands and their rhodium (I) complexes with carbohydrates as chiral groups". . p. 115 - 121. Retrieved 1996.
• 4、 Ghosh, Arun K.,Reddy, Guddeti Chandrashekar,Kovela, Satish,Relitti, Nicola,Urabe, Veronica K.,Prichard, Beth E.,Jurica, Melissa S.. "Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity". . p. 7293 - 7297. Retrieved 2018.
• 5、 Ghosh, Arun K.,Veitschegger, Anne M.,Nie, Shenyou,Relitti, Nicola,Macrae, Andrew J.,Jurica, Melissa S.. "Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition". . p. 5187 - 5198. Retrieved 2018.
• 6、 Fetizon, M.,Khac, Duc Do,Tho, Nguyen Dinh. "AN APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE TRICHOTHECENES FROM TRI-O-ACETYL-D-GLUCAL". . p. 1777 - 1780. Retrieved 1986.
• 7、 David,Malleron,Cavaye. "Some derivatives of 3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (KDN)". . p. 233 - 241. Retrieved 1994.
• 8、 Torii, Sigeru,Inokuchi, Tsutomu,Masatsugu, Yoshinori. "A Straightforward Access to 5-Deoxy-D-arabinono-1,4-lactone, a Versatile Intermediate in the Lauraceae Lactones Syntheses". . p. 3629 - 3630. Retrieved 1985.
• 9、 Xu, Wenke,Yang, Hui,Liu, Yingju,Hua, Yingchun,He, Bin,Ning, Xin,Qin, Zhiyan,Liu, Hong-Min,Liu, Feng-Wu. "Facile Approaches to 2-Deoxy- d -glucose and 2-Deoxy-α- d -glucopyranonucleosides from d -Glucal". . p. 3686 - 3691. Retrieved 2017.
• 10、 Anquetin, Guillaume,Rawe, Sarah L.,McMahon, Kevin,Murphy, Evelyn P.,Murphy, Paul V.. "Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal". . p. 1592 - 1600. Retrieved 2008.