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
• General Description: D-Glucal is a versatile carbohydrate derivative used as a key starting material in organic synthesis, particularly for constructing complex bioactive molecules. It serves as a precursor in the synthesis of cytotoxic eleutheside templates and the formal synthesis of (-)-morphine, demonstrating its utility in stereoselective transformations such as Grignard additions, epoxide formations, and cascade Claisen rearrangements. Its structural flexibility enables the formation of critical intermediates, including epoxy allylic alcohols and phenanthrofuran skeletons, highlighting its importance in medicinal chemistry and natural product synthesis.

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

4,6-O-benzylidene-D-allal

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

Downstream raw materials:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

1,5,6,6-tetramethoxy-hexan-3-one

D-lactal

(2R,3S,4R,4aR,5S,10S,10aS)-10-Dimethoxymethyl-5-(2,4-dinitro-phenylamino)-2-hydroxymethyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]chromene-3,4-diol

Refernces

Synthesis of a C(4)-C(9) eleutheside template from D-glucal

10.1016/S0040-4020(00)01117-0

The research focuses on the synthesis of a C(4)-C(9) eleutheside template from D-glucal, with the aim of creating potential C(4)-C(9) templates for eleutheside syntheses, which are of interest due to their cytotoxic properties and potential as cancer therapeutics. The study employs an eight-step sequence that includes a stereoselective methyl Grignard addition to an iodo-hexenulosec and an epoxide formation via intramolecular iodide displacement. Key chemicals used in the process include D-glucal, LiBH4 in n-octanol for an unusual hemiacetal reduction protocol, and various bases and solvents to facilitate the reactions. The synthesis of epoxy allylic alcohol 4 and the corresponding aldehyde (Z)-14 were achieved, setting the stage for further eleutheside core synthesis. The overall yield of the eight-step synthesis from D-glucal was 17%, and the researchers are currently examining the elaboration of 4 via epoxide cleavage reactions and using aldehyde 14 for chain extensions at C(4).

Formal synthesis of (-)-morphine from d-glucal based on the cascade Claisen rearrangement

10.1016/j.tetlet.2007.11.037

The research centers on the formal synthesis of (-)-morphine, commencing from D-glucal. The core experimental procedures involve the preparation of the C-ring using Ferrier's carbocyclization reaction and the stereoselective generation of adjacent tertiary and quaternary carbons in the C-ring through a cascade Claisen rearrangement. The synthesis sequence includes a Suzuki-Miyaura coupling to form an intermediate, followed by the crucial cascade Claisen rearrangement to construct the adjacent tertiary and quaternary carbons, which are integral to the morphine structure. Subsequently, an intramolecular Friedel-Crafts type reaction is employed to build the ABCE-phenanthrofuran skeleton, and the introduction of a tosylamide function precedes a reductive cyclization to yield (-)-dihydroisocodeine, a known synthetic intermediate for (-)-morphine. Various analytical techniques, such as nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, mass spectrometry (MS), and elemental analysis, are utilized to characterize the newly synthesized compounds. The reactants encompass a range of organic acids, alkali metals, organic boronic acids, and D-glucal derivatives.