.alpha.-D-Glucopyranose, 1,2-O-(1S)-1-methoxyethylidene-, triacetate

Base Information

• Chemical Name: .alpha.-D-Glucopyranose, 1,2-O-(1S)-1-methoxyethylidene-, triacetate
• CAS No.: 64727-27-1
• Molecular Formula: C15H22 O10
• Molecular Weight: 362.334
• Mol file: 64727-27-1.mol

Synonyms:a-D-Glucopyranose,1,2-O-(1-methoxyethylidene)-, triacetate, (S)-; 5H-1,3-Dioxolo[4,5-b]pyran, a-D-glucopyranose deriv.

Chemical Property of .alpha.-D-Glucopyranose, 1,2-O-(1S)-1-methoxyethylidene-, triacetate

Chemical Property:

• PSA: 115.82000
• LogP: -0.12670

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .alpha.-D-Glucopyranose, 1,2-O-(1S)-1-methoxyethylidene-, triacetate

There total 5 articles about .alpha.-D-Glucopyranose, 1,2-O-(1S)-1-methoxyethylidene-, triacetate 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: 48.0%

methanol (67-56-1) + p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → 3,4,6-tri-O-acetyl-1,2-O-[1-(exo-methoxy)ethylidene]-alpha-D-glucopyranose (64727-27-1) + methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6)

Guidance literature:

With 3 A molecular sieve; In acetonitrile; Yields of byproduct given; electrochemical synthesis: one compartment, three-electrode, air-tight cell, vitrous carbon anode and Pt catode, 0.2 M LiBF₄ as supporting electrolyte, constant potential 1.45 V (vs standard calomel reference electrode);

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

(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose