1 2-O-(1-ETHOXYETHYLIDENE)-BETA-D-MANNO&

Base Information

• Chemical Name: 1 2-O-(1-ETHOXYETHYLIDENE)-BETA-D-MANNO&
• CAS No.: 28140-37-6
• Molecular Formula: C16H24O10
• Molecular Weight: 376.361
• Hs Code.: 29400090
• Mol file: 28140-37-6.mol

Synonyms:Mannopyranose,cyclic 1,2-(ethyl orthoacetate) 3,4,6-triacetate, b-D- (8CI);Orthoacetic acid, cyclic ester with b-D-mannopyranose 3,4,6-triacetate, ethyl ester (8CI);NSC 267968;

Chemical Property of 1 2-O-(1-ETHOXYETHYLIDENE)-BETA-D-MANNO&

Chemical Property:

• Vapor Pressure: 1.13E-07mmHg at 25°C
• Melting Point: 101-103 °C
• Refractive Index: 1.49
• Boiling Point: 432.174 °C at 760 mmHg
• Flash Point: 187.536 °C
• PSA: 115.82000
• Density: 1.289 g/cm³
• LogP: 0.26340

Purity/Quality:

99% ^*data from raw suppliers

3,4,6-Tri-O-acetyl-1,2-O-ethoxyethylidene-b-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of 1 2-O-(1-ETHOXYETHYLIDENE)-BETA-D-MANNO&

There total 13 articles about 1 2-O-(1-ETHOXYETHYLIDENE)-BETA-D-MANNO& 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: 90.0%

ethanol (64-17-5) + acetobromomannose (13242-53-0) → 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside (28140-37-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 4h;

DOI:10.1021/jo0478609

Reference yield: 70.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + ethanol (64-17-5) → 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside (28140-37-6)

Guidance literature:

With teterabutylammonium; lutidine; In chloroform; at 45 ℃; for 24h;

DOI:10.1021/jo00352a012

Reference yield:

→ Tri-O-acetyl-α-D-glucopyranose-1,2- (3254-15-7,3254-17-9,19189-53-8,28140-37-6,29907-27-5,38081-38-8,63950-42-5,65336-76-7,70749-16-5,92937-14-9,93601-64-0,93601-65-1,127910-77-4)

Guidance literature:

Tetra-O-acetyl-α-D-glucopyranosylbromid, Erwaermen mit A. in sym.-Collidin, Ggw. von Tetra-butyl-ammonium-bromid;

DOI:10.1139/v65-298

upstream raw materials:

acetobromomannose

D-Mannose pentaacetate

ethanol

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide

Downstream raw materials:

tert-butyl-dimethylsilyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

ethyl 3,4,6-tri-O-benzyl-2-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

ethyl 3,4,6-tri-O-benzyl-2-O-(tert-butyldimethylsilyl)-1-thio-β-D-mannopyranoside

Refernces

• 1、 Wawryszyn, Mirella,Sauter, Paul F.,Nieger, Martin,Koos, Martin R. M.,Koehler, Christine,Luy, Burkhard,Lemke, Edward A.,Br?se, Stefan. "Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins". supporting information. p. 4296 - 4305. Retrieved 2018/08/29.
• 2、 Chen, Liqun,Tan, Zhongping. "A convenient and efficient synthetic approach to mono-, di-, and tri-O-mannosylated Fmoc amino acids". supporting information. p. 2190 - 2193. Retrieved 2013/04/24.