Maltosan

Base Information

• Chemical Name: Maltosan
• CAS No.: 6983-27-3
• Molecular Formula: C₁₂H₂₀O₁₀
• Molecular Weight: 324.285
• Hs Code.: 2940000080
• Mol file: 6983-27-3.mol

Synonyms:1,6-anhydro maltose;(2R,3R,4S,5S,6R)-2-((1R,2S,3R,4R,5R)-3,4-Dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol;Maltosan;

Chemical Property of Maltosan

Chemical Property:

• Melting Point: 145-150 °C (decomp)
• Boiling Point: 640.3±55.0 °C(Predicted)
• PSA: 158.30000
• Density: 1.74±0.1 g/cm3(Predicted)
• LogP: -4.35160

Purity/Quality:

99%, ^*data from raw suppliers

Maltosan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Maltosan

There total 19 articles about Maltosan 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: 100.0%

(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol (86461-99-6,113842-60-7) → 1,6-anhydromaltose (2672-63-1,6983-27-3,34395-01-2,35405-71-1,56907-28-9,61117-13-3,78215-49-3,80795-18-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 80 ℃; for 0.5h;

DOI:10.1016/0008-6215(87)80136-2

Reference yield: 42.0%

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose (28868-67-9) → 1,6-anhydro-β-maltose (6983-27-3)

Guidance literature:

With sodium methylate; In methanol;

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-4-O-<(trifluormethyl)sulfonyl>-β-D-galactopyranose (104976-44-5) → (2R,3S,4S,5S,6R)-2-((1R,2S,3R,4R,5R)-3,4-Dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (2672-63-1,6983-27-3,34395-01-2,35405-71-1,56907-28-9,61117-13-3,78215-49-3,80795-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / NaH / hexamethylphosphoric acid triamide; dimethylformamide / 1.) -10 deg C, 15 min, 2.) 2.5 h

2: H₂, AcOH / Pd/C / ethanol / 3 h

With hydrogen; sodium hydride; acetic acid; palladium on activated charcoal; In N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

hepta-O-acetyl-di-N-methyl-β-maltosylamine

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose

1,6-Anhydro-2,3-di-O-benzyl-4-O-<(trifluormethyl)sulfonyl>-β-D-galactopyranose

2,3,4-Tri-O-benzyl-6-O-(monomethoxytrityl)-D-mannose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose

1,6-anhydro-4-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-allopyranosyl)-3-O-benzyl-2-O-(p-methoxybenzyl)-β-D-glucopyranose

Refernces

• 1、 Lepage, Mathieu L.,Bodlenner, Anne,Compain, Philippe. "Stereoselective synthesis of α-glycosyl azides by TMSOTf-mediated ring opening of 1,6-anhydro sugars". . p. 1963 - 1972. Retrieved 2013/05/21.
• 2、 Tsvetkov, Yury E.,Klotz, Wolfgang,Schmidt, Richard R.. "Anomeric O-Alkylation, 9. Disaccharide Synthesis via Anomeric O-Alkylation". . p. 371 - 376. Retrieved 2007/10/02.