METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE

Base Information

• Chemical Name: METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE
• CAS No.: 50705-56-1
• Molecular Formula: C₁₃H₂₂O₆
• Molecular Weight: 274.314
• Hs Code.: 2938909090
• Mol file: 50705-56-1.mol

Synonyms:METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE

Chemical Property of METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 0.000323mmHg at 25°C
• Melting Point: 75 °C
• Refractive Index: 1.494
• Boiling Point: 330.3°C at 760 mmHg
• Flash Point: 130.3°C
• PSA: 55.38000
• Density: 1.2g/cm³
• LogP: 1.02930

Purity/Quality:

98% ^*data from raw suppliers

Methyl2,3:4,6-Di-O-isopropylidene-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2,3:4,6-Di-O-isopropylidene-mannopyranoside is prepared from Me α-D-mannopyranosidea and used to synthesize Me 6-O-benzoyl-2,3-O-isopropylidene-α-D-talopyranoside. Also, it is a protected sugar (mannose) building block.

Technology Process of METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE

There total 13 articles about METHYL-2,3:4,6-DI-O-ISOPROPYLIDENE-D-MANNOPYRANOSIDE 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: 92.0%

2,2-dimethoxy-propane (77-76-9) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside (13035-60-4,50705-56-1,75100-00-4,89387-76-8,118542-52-2,118542-53-3,143996-47-8,143996-48-9)

Guidance literature:

With sulfuric acid; In acetonitrile; at 20 ℃; for 0.75h;

DOI:10.1016/j.tetlet.2006.04.118

Reference yield: 49.0%

2-Methoxypropene (116-11-0) + talopyranose (530-25-6) → methyl 2,3:4,6-di-O-isopropylidene-β-D-talopyranoside (13035-60-4,50705-56-1,75100-00-4,89387-76-8,118542-52-2,118542-53-3,143996-47-8,143996-48-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)89859-8

Reference yield: 45.0%

methyl 4,6-O-isopropylidene-α-D-mannopyranoside (63167-67-9) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) + methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside (13035-60-4,50705-56-1,75100-00-4,89387-76-8,118542-52-2,118542-53-3,143996-47-8,143996-48-9)

Guidance literature:

With methyl iodide; at 80 ℃; for 14h;

upstream raw materials:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

methyl 2,3-O-isopropylidene-α-D-mannopyranoside

methanol

C₁₈H₃₇N₃O₆P⁽¹⁺⁾*Cl^(1-)

Downstream raw materials:

methyl 2,3-O-isopropylidene-α-D-mannopyranoside

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside

methyl 4,6-di-O-benzyl-α-D-mannopyranoside

Refernces

• 1、 Neogi, Arpita,Majhi, Tirtha P.,Achari, Basudeb,Chattopadhyay, Partha. "Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines". . p. 330 - 336. Retrieved 2008/09/18.
• 2、 Burger, Irmgard,Burger, Barend V.,Albrecht, Carl F.,Spies, Hendrik S. C.,Sandor, Peter. "Triterpenoid saponins from Becium grandiflorum var. obovatum". . p. 2087 - 2095. Retrieved 2007/10/03.