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.: 3254-16-8
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.334
• Mol file: 3254-16-8.mol

Synonyms:Glucopyranose,cyclic 1,2-(methyl orthoacetate) 3,4,6-triacetate, a-D- (7CI,8CI); 5H-1,3-Dioxolo[4,5-b]pyran, a-D-glucopyranose deriv.;Orthoacetic acid, cyclic ester with a-D-glucopyranose 3,4,6-triacetate, methyl ester;1,2-Methylorthoacetyl-3,4,6-tri-O-acetyl-a-D-glucopyranose;3,4,6-Tri-O-acetyl-1,2-O-methylorthoacetyl-a-D-glucopyranose

Chemical Property of 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)

Chemical Property:

• Boiling Point: 419.1±45.0 °C(Predicted)
• PSA: 115.82000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: -0.12670

Purity/Quality:

98% ^*data from raw suppliers

3,4,6-Tri-o-acetyl-1,2-o-(1-methoxyethylidene)-beta-D-mannopyranose 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)

There total 3 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

2,3,4,6-tetra-O-acetyl-1-(methoxycarbonylmethyl)thio-α-D-mannopyranoside

methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

2,3,4,6-tetra-O-acetyl-β-D-mannopyranose

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.