1,3,4-tri-O-acetyl-2,6-dideoxyhexopyranose

Base Information

• Chemical Name: 1,3,4-tri-O-acetyl-2,6-dideoxyhexopyranose
• CAS No.: 33985-27-2
• Molecular Formula: C12H18 O7
• Molecular Weight: 274.2671
• Mol file: 33985-27-2.mol

Synonyms:L-lyxo-Hexopyranose,2,6-dideoxy-, triacetate, a- (8CI); NSC 287064

Chemical Property of 1,3,4-tri-O-acetyl-2,6-dideoxyhexopyranose

Chemical Property:

• Vapor Pressure: 0.00014mmHg at 25°C
• Boiling Point: 333.1°Cat760mmHg
• Flash Point: 143.7°C
• Density: 1.21g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3,4-tri-O-acetyl-2,6-dideoxyhexopyranose

There total 11 articles about 1,3,4-tri-O-acetyl-2,6-dideoxyhexopyranose 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: 89.0%

acetic acid (64-19-7,77671-22-8) + 3,4-di-O-acetyl-L-fucal (54621-94-2) → (2S,4S,5R,6S)-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate (33985-27-2)

Guidance literature:

With methanesulfonic acid; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(82)80020-7

Reference yield: 85.0%

2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide (16741-27-8) → (2S,4S,5R,6S)-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate (33985-27-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In Isopropyl acetate; at 20 ℃; for 20h; regioselective reaction; Sealed tube; Irradiation; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.0c11209

Reference yield: 54.0%

2,6-dideoxy-D-xylo-hexose (2053-00-1,17050-70-3,22899-74-7,25029-50-9,45742-39-0,45742-40-3,49871-87-6,51020-42-9,62413-93-8,71328-50-2,74112-04-2,74112-05-3,74112-09-7,74112-10-0,74112-11-1,74112-14-4,78185-01-0,78185-02-1,89253-95-2,89253-96-3,89253-97-4,97276-35-2,102850-49-7,102850-50-0,110043-58-8,138458-66-9,138458-67-0,139630-51-6,139683-22-0) + acetic anhydride (108-24-7) → 1,3,4-tri-O-acetyl-2,6-dideoxy-D-xylo-hexopyranose (33985-27-2,33985-28-3,33985-29-4,57794-09-9,67335-77-7,71155-55-0,71155-56-1,71155-58-3,74112-06-4,74112-07-5,74112-08-6,74112-12-2,74112-13-3,74163-99-8,83059-25-0,84129-81-7,84129-82-8,89063-61-6,108942-62-7,113829-49-5)

Guidance literature:

dmap; In pyridine; for 18h;

DOI:10.1016/S0040-4020(01)80790-0

upstream raw materials:

2,6-dideoxy-D-xylo-hexose

acetic anhydride

(2R,3S,4S)-hept-6-ene-2,3,4-triol

methyl 2,3,6-trideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

Downstream raw materials:

2,6-dichlorophenyl<4-O-acetyl-2,6-dideoxy-3-O-(4-methoxybenzyl)-α-L-galactopyranosyl>-(1->4)-2,6-dideoxy-3-O-(4-methoxybenzyl)-1-thio-α-L-galactopyranoside

2,6-dichlorophenyl<2,6-dideoxy-3-O-(4-methoxybenzyl)-α-L-galactopyranosyl>-(1->4)-2,6-dideoxy-3-O-(4-methoxybenzyl)-1-thio-α-L-galactopyranoside

2,6-dichlorophenyl 2,6-dideoxy-3-O-(4-methoxybenzyl)-1-thio-α-L-galactopyranoside

2,6-dichlorophenyl 2,6-dideoxy-1-thio-α-L-galactopyranoside

Refernces

• 1、 -. "METHODS AND COMPOSITIONS FOR MAKING ANTIBODIES AND ANTIBODY DERIVATIVES WITH REDUCED CORE FUCOSYLATION". Page/Page column. . Retrieved 2014/01/23.
• 2、 -. "Methods and compositions for making antibodies and antibody derivatives with reduced core fucosylation". . . Retrieved 2012/05/04.