3,4,6-Tri-O-acetyl-alpha-D-galactopyranose 1,2-(methyl orthoacetate)

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-alpha-D-galactopyranose 1,2-(methyl orthoacetate)
• CAS No.: 50801-29-1
• Molecular Formula: C15H22 O10
• Molecular Weight: 362.334
• Mol file: 50801-29-1.mol

Synonyms:5H-1,3-Dioxolo[4,5-b]pyran,a-D-galactopyranose deriv.

Chemical Property of 3,4,6-Tri-O-acetyl-alpha-D-galactopyranose 1,2-(methyl orthoacetate)

Chemical Property:

• Vapor Pressure: 3.13E-07mmHg at 25°C
• Boiling Point: 419.1oC at 760 mmHg
• Flash Point: 182.5oC
• PSA: 115.82000
• Density: 1.31g/cm3
• LogP: -0.12670
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4,6-Tri-O-acetyl-α-D-galactopyranose1,2-(MethylOrthoacetate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,4,6-Tri-O-acetyl-α-D-galactopyranose 1,2-(Methyl Orthoacetate) (cas# 50801-29-1) is a compound useful in organic synthesis.

Technology Process of 3,4,6-Tri-O-acetyl-alpha-D-galactopyranose 1,2-(methyl orthoacetate)

There total 4 articles about 3,4,6-Tri-O-acetyl-alpha-D-galactopyranose 1,2-(methyl orthoacetate) 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: 84.0%

methanol (67-56-1) + (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate (66118-22-7) → 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) + tetra-O-acetyl-1-O-methyl-β-D-glucopyranose (604-70-6,4860-85-9,5019-22-7,5019-23-8,5019-24-9,5019-25-0,14795-19-8,17460-42-3,19189-52-7,25217-94-1,34254-54-1,39598-81-7,39598-82-8,39598-85-1,39598-86-2,39598-90-8,39598-92-0,41398-87-2,51819-80-8,51819-84-2,51819-85-3,51819-86-4,51897-78-0,73136-69-3,75880-73-8,92619-79-9,92934-57-1,92934-58-2,114298-54-3,128657-15-8,132562-65-3,141042-95-7,30657-67-1)

Guidance literature:

silver(I) chloride; In acetonitrile; for 3h; Heating;

Reference yield: 78.0%

2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (529493-92-3) + tributyltin methoxide (1067-52-3) → Acetic acid 6-acetoxy-5-acetoxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) + tributyltin bromide (1461-23-0)

Guidance literature:

With (N(C₂H₅)4)Br; 1:1:0.5; 45°C; 20 h;

Reference yield:

methanol (67-56-1) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride (4451-36-9) → 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver nitrate; In acetonitrile; for 4h; Product distribution; Ambient temperature; presence or absence of silver salts;

DOI:10.1016/0008-6215(85)85014-X

upstream raw materials:

methanol

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride

2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose

2,3,4,6-tetra-O-acetyl-1-O-(cyclohexylcarbonyl)-β-D-glucopyranose

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene

Refernces

• 1、 Tsui, David S. K.,Gorin, Philip A. J.. "Methods for the preparation of alkyl 1,2-orthoacetates of D-glucopyranose and D-galactopyranose in high yield". . p. 137 - 147. Retrieved 2007/10/02.