BENZYL 5-AMINO-5-DEOXY-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE

Base Information

• Chemical Name: BENZYL 5-AMINO-5-DEOXY-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE
• CAS No.: 91364-19-1
• Molecular Formula: C16H23 N O5
• Molecular Weight: 309.362
• Mol file: 91364-19-1.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,a-D-mannofuranoside deriv.

Chemical Property of BENZYL 5-AMINO-5-DEOXY-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 468.991°C at 760 mmHg
• Flash Point: 237.437°C
• PSA: 83.17000
• Density: 1.259g/cm³
• LogP: 1.46810

Purity/Quality:

98%Min ^*data from raw suppliers

Benzyl 5-amino-5-deoxy-2,3-O-isopropylidene-a-D-mannofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZYL 5-AMINO-5-DEOXY-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE

There total 9 articles about BENZYL 5-AMINO-5-DEOXY-2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE 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: 90.0%

5-azido-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose (94119-03-6) → 5-amino-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose (91364-19-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃;

DOI:10.1002/adsc.201600903

Reference yield:

1-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-trityloxy-ethanone oxime (91364-14-6) → 5-amino-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose (91364-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.3 g / H₂ / Raney nickel

2: 0.5M HCl, H₂O / methanol / 18 h / Ambient temperature

With hydrogenchloride; water; hydrogen; nickel; In methanol;

DOI:10.1016/0008-6215(84)85084-3

Reference yield:

5,6-di-O-acetyl-1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose (94152-34-8) → 5-amino-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose (91364-19-1)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / water; methanol / 20 °C

2: pyridine / 36 h / 20 °C

3: pyridine / dichloromethane / -25 - 20 °C

4: 18-crown-6 ether; sodium azide / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C

5: boron trifluoride diethyl etherate / dichloromethane; methanol / 1.5 h / 0 - 20 °C

6: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium carbonate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/adsc.201600903

upstream raw materials:

1-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-trityloxy-ethanone oxime

1-O-benzyl-2,3-O-isopropylidene-5,6-di-O-mesyl-α-D-mannofuranose

5,6-di-O-acetyl-1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose

1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose

Refernces

• 1、 Legler, Guenter,Juelich, Elisabeth. "SYNTHESIS OF 5-AMINO-5-DEOXY-D-MANNOPYRANOSE AND 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL, AND INHIBITION OF α- AND β-D-MANNOSIDASES". . p. 61 - 72. Retrieved 2007/10/02.