.beta.-D-Gulopyranose, 3-amino-1,6-anhydro-3-deoxy-, hydrochloride

Base Information

• Chemical Name: .beta.-D-Gulopyranose, 3-amino-1,6-anhydro-3-deoxy-, hydrochloride
• CAS No.: 108782-66-7
• Molecular Formula: C₆H₁₁NO₄*ClH
• Molecular Weight: 197.619
• Mol file: 108782-66-7.mol

Synonyms:6,8-Dioxabicyclo[3.2.1]octane,b-D-gulopyranose deriv.

Chemical Property of .beta.-D-Gulopyranose, 3-amino-1,6-anhydro-3-deoxy-, hydrochloride

Chemical Property:

• PSA: 84.94000
• LogP: -0.70710

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Gulopyranose, 3-amino-1,6-anhydro-3-deoxy-, hydrochloride

There total 3 articles about .beta.-D-Gulopyranose, 3-amino-1,6-anhydro-3-deoxy-, hydrochloride 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: 49.0%

3-amino-1,6-anhydro-4-O-benzoyl-3-deoxy-β-D-gulopyranose 2O,3N-trichloroacetimidate (108782-57-6) → 3-amino-1,6-anhydro-3-deoxy-β-D-gulopyranose hydrochloride (108782-66-7)

Guidance literature:

With sodium hydroxide; In methanol; water; for 2h; Heating;

Reference yield:

1,6-anhydro-3-deoxy-3-nitro-β-D-gulopyranose (116607-29-5) → 3-amino-1,6-anhydro-3-deoxy-β-D-gulopyranose hydrochloride (108782-66-7)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; under 2585.74 Torr;

DOI:10.1016/S0040-4020(99)00327-0

Reference yield:

(2R)-[1,3]dioxolane-2r,4c-dicarbaldehyde (127903-51-9) → 3-amino-1,6-anhydro-3-deoxy-β-D-gulopyranose hydrochloride (108782-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / NaOMe / methanol

2: H₂; aq. HCl / Pd/C / 2585.74 Torr

With hydrogenchloride; hydrogen; sodium methylate; palladium on activated charcoal; In methanol; 1: Cyclization / 2: Reduction;

DOI:10.1016/S0040-4020(99)00327-0

upstream raw materials:

3-amino-1,6-anhydro-4-O-benzoyl-3-deoxy-β-D-gulopyranose 2O,3N-trichloroacetimidate

1,6-anhydro-3-deoxy-3-nitro-β-D-gulopyranose

(2R)-[1,3]dioxolane-2r,4c-dicarbaldehyde

Downstream raw materials:

1,6-anhydro-3-N-benzylamino-2-O,3-N-carbonyl-3-deoxy-β-D-gulopyranose

4-O-acetyl-3-amino-1,6-anhydro-3-deoxy-β-D-gulopyranose 2-phosphate

3-amino-1,6-anhydro-3-N-benzyl-3-deoxy-4-O-(2-tetrahydropyranyl)-β-D-gulopyranose

1,6-anhydro-3-N-benzylamino-2-O,3-N-carbonyl-3-deoxy-4-O-(2-tetrahydropyranyl)-β-D-gulopyranose

Refernces

• 1、 Jacobsen, Steffen. "Dioxolanylium Ions Derived from Carbohydrates. X. Nucleophilic trans Opening with the Trichloroacetimidoyl Neighbouring Group". . p. 493 - 497. Retrieved 2007/10/02.