3,6-Dideoxy-D-arabino-hexose

Base Information

• Chemical Name: 3,6-Dideoxy-D-arabino-hexose
• CAS No.: 5658-12-8
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• Mol file: 5658-12-8.mol

Synonyms:D-arabino-Hexose, 3,6-dideoxy-;(2S,4R,5R)-2,4,5-trihydroxyhexanal;3,6-Dideoxy-D-arabino-hexose;3,6-dideoxy-D-mannose

Chemical Property of 3,6-Dideoxy-D-arabino-hexose

Chemical Property:

• Vapor Pressure: 8.28E-07mmHg at 25°C
• Melting Point: NA
• Boiling Point: 365°Cat760mmHg
• PKA: 13.08±0.20(Predicted)
• Flash Point: 188.8°C
• PSA: 69.92000
• Density: 1.249g/cm³
• LogP: -1.16460
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 104

Purity/Quality:

95% ^*data from raw suppliers

Tyvelose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CC(C=O)O)O)O
• Isomeric SMILES: C[C@H]([C@@H](C[C@@H](C=O)O)O)O
• Description: Tyvelose is an unusual 3,6-dideoxyhexose terminal sugar and the immunodominant component of glycoprotein antigens in the parasitic helminth T. spiralis, which is responsible for trichinosis in humans. It is produced in high amounts by the infective larva and is immunodominant during the muscle stage of infection. Mice immunized with tyvelose-BSA produce IgG1 antibodies to tyvelose but are not resistant to infection by T. spiralis. Tyvelose-specific antibodies (2.5 mg/20 g) administered to rat pups leads to expulsion of first stage larvae from the intestine within one hour.
• Uses: The unusual sugar Tyvelose is the immunodominant portion of the major larval glycoprotein antigens of Trichinella spiralis, which play an important role in generating immunity against the intestinal stages of infection.

Technology Process of 3,6-Dideoxy-D-arabino-hexose

There total 3 articles about 3,6-Dideoxy-D-arabino-hexose 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:

O6-(toluene-4-sulfonyl)-D-arabino-3-deoxy-hexose dimethyl dithioacetal (98979-92-1) → D-arabino-3,6-dideoxy-hexose (5658-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / dioxane

2: (i) HgO, aq. acetone, (ii) HgCl₂

With lithium aluminium tetrahydride; In 1,4-dioxane;

Reference yield:

methyl (R)-3-deoxy-α-D-arabinohexopyranose (6198-74-9,24332-89-6,26922-85-0,28034-64-2,29073-92-5,29581-42-8,35521-82-5,115888-69-2,115936-03-3,117893-41-1) → D-arabino-3,6-dideoxy-hexose (5658-12-8)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; Erwaermen einer Loesung des Reaktionsprodukts in Benzol und Aether mit Lithiumalanat und Erhitzen des danach isolierten Reaktionsprodukts mit wss.Salzsaeure;

Reference yield:

D-arabino-3,6-dideoxy-hexose dimethyl dithioacetal (94892-83-8) → D-arabino-3,6-dideoxy-hexose (5658-12-8)

Guidance literature:

Multistep reaction; (i) HgO, aq. acetone, (ii) HgCl₂;

upstream raw materials:

methyl (R)-3-deoxy-α-D-arabinohexopyranose

D-arabino-3,6-dideoxy-hexose dimethyl dithioacetal

O⁶-(toluene-4-sulfonyl)-D-arabino-3-deoxy-hexose dimethyl dithioacetal