Methyla-D-laminarabiosideheptaacetate

Base Information

• Chemical Name: Methyla-D-laminarabiosideheptaacetate
• CAS No.: 7322-42-1
• Molecular Formula: C₂₇H₃₈O₁₈
• Molecular Weight: 650.588
• Mol file: 7322-42-1.mol

Synonyms:Methyla-D-laminarabiosideheptaacetate;Methyl 3-O-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside Triacetate

Chemical Property of Methyla-D-laminarabiosideheptaacetate

Chemical Property:

• Melting Point: 188-189°C
• Boiling Point: 649.8±55.0 °C(Predicted)
• PSA: 221.02000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: -0.74750

Purity/Quality:

98% ^*data from raw suppliers

Methyl a-D-laminarabioside heptaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl-α-D-laminaribioside Heptaacetate (cas# 7322-42-1) is a compound useful in organic synthesis.

Technology Process of Methyla-D-laminarabiosideheptaacetate

There total 14 articles about Methyla-D-laminarabiosideheptaacetate 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: 55.0%

3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose (52443-08-0) + Methyl 2,4,6-Tri-O-acetyl-3-O-trityl-β-D-galactopyranoside (122926-87-8) → Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-methoxy-4-((3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (7322-42-1,66583-05-9,71080-24-5,71978-79-5,84039-39-4,84039-43-0,85372-94-7,101072-34-8,101072-35-9,102854-37-5,117561-24-7,122926-93-6,145251-15-6,145251-16-7)

Guidance literature:

With triphenylmethylium trifluoromethansulfonate; In dichloromethane; at 20 ℃; for 17h;

Reference yield:

methyl β-D-glucopyranosyl-<1->3>-α-D-glucopyranoside (7115-19-7) + acetic anhydride (108-24-7) → methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-α-D-galactopyranoside (7322-42-1)

Guidance literature:

With pyridine;

Reference yield:

ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-propargyl-1-thio-β-D-glucopyranoside (1425503-73-6) → methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-α-D-galactopyranoside (7322-42-1)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / dichloromethane / 12 h / 20 °C

2: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / -40 - 20 °C / Inert atmosphere

3: ammonia; sodium / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

4: pyridine; dmap / 12 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; copper(l) iodide; trifluorormethanesulfonic acid; ammonia; sodium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201201076

upstream raw materials:

methyl β-D-glucopyranosyl-<1->3>-α-D-glucopyranoside

acetic anhydride

ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-propargyl-1-thio-β-D-glucopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Refernces

• 1、 Mueller, Matthias,Huchel, Ursula,Geyer, Armin,Schmidt, Richard R.. "Efficient Intramolecular Glycosylation Supported by a Rigid Spacer". . p. 6190 - 6201. Retrieved 2007/10/03.
• 2、 Betaneli, V. I.,Kryazhevskikh, I. A.,Kochetkov, N. K.. "GLYCOSYLATION OF 1,2-O-CYANOBENZYLIDENE DERIVATIVES OF SUGARS. INFLUENCE OF REACTION PROMOTER AND SOLVENT". . p. 12 - 14. Retrieved 2007/10/02.