3-O-Acetyl-4,6-O-benzylidene-D-glucal

Base Information

• Chemical Name: 3-O-Acetyl-4,6-O-benzylidene-D-glucal
• CAS No.: 14125-71-4
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• DSSTox Substance ID: DTXSID501135823
• Nikkaji Number: J1.520.302A,J744.545H
• Mol file: 14125-71-4.mol

Synonyms:3-O-ACETYL-4,6-O-BENZYLIDENE-D-GLUCAL;14125-71-4;DTXSID501135823;V10211;3-O-Acetyl-4-O,6-O-benzylidene-1,2-dideoxy-D-arabino-1-hexenopyranose;1,5-Anhydro-3-O-acetyl-4-O,6-O-benzylidene-2-deoxy-D-arabino-hexa-1-enitol;D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-4,6-O-(phenylmethylene)-, 3-acetate

Chemical Property of 3-O-Acetyl-4,6-O-benzylidene-D-glucal

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 276.09977361
• Heavy Atom Count: 20
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

3-O-ACETYL-4,6-O-BENZYLIDENE-D-GLUCAL 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1C=COC2C1OC(OC2)C3=CC=CC=C3
• Isomeric SMILES: CC(=O)O[C@@H]1C=CO[C@H]2[C@H]1OC(OC2)C3=CC=CC=C3

Technology Process of 3-O-Acetyl-4,6-O-benzylidene-D-glucal

There total 5 articles about 3-O-Acetyl-4,6-O-benzylidene-D-glucal 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: 91.0%

2,3-di-O-acetyl-4,6-o-benzylidene-α-D-glucopyranosyl bromide (143995-54-4) → 3-O-acetyl-4.6-O-benzylidene-D-arabino-hex-1-enitol (14125-71-4)

Guidance literature:

With bis(cyclopentadienyl)-titanium(III) chloride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4039(96)00865-9

Reference yield: 9.4%

acetic anhydride (108-24-7) + methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (2880-96-8,3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2) → methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside (19465-06-6,68907-47-1,75879-81-1,75879-82-2,75879-83-3,101978-79-4,130061-59-5) + 3-O-acetyl-4,6-O-benzylidene-1,2-dideoxy-D-ribohex-1-enopyranose (5987-34-8,14125-71-4,72074-91-0,74708-02-4,83151-51-3,131432-51-4)

Guidance literature:

With copper(l) iodide; methyllithium; Yield given. Multistep reaction; 1.) diethyl ether, 0 deg C, 1 h; 2.) pyridine;

Reference yield:

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside (257925-66-9) → 3-O-acetyl-4.6-O-benzylidene-D-arabino-hex-1-enitol (14125-71-4)

Guidance literature:

Multi-step reaction with 2 steps

2: 91 percent / 2TiCl>2 / Ambient temperature

With bis(cyclopentadienyl)-titanium(III) chloride;

DOI:10.1021/jo982447k

upstream raw materials:

2,3-di-O-acetyl-4,6-o-benzylidene-α-D-glucopyranosyl bromide

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside

acetic anhydride

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside

Downstream raw materials:

Acetic acid (4aR,6R,7S,8S,8aR)-6,7-dichloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

4-chlorobutyl 3-O-acetyl-4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside

Acetic acid (4aR,6R,7R,8S,8aR)-7-chloro-6-(4-chloro-butoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

(4S,5R)-4-((E)-Buta-1,3-dienyl)-2-phenyl-[1,3]dioxan-5-ol