ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 197853-41-1
• Molecular Formula: C₂₉H₃₂O₅S
• Molecular Weight: 492.636
• Mol file: 197853-41-1.mol

Synonyms:ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 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: 99.0%

benzyl bromide (100-39-0) + ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (197853-41-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo4003135

Reference yield:

ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (197853-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH

2: TBAI; NaH

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid;

DOI:10.1055/s-2003-40351

Reference yield:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (197853-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol; sodium methylate / 0.5 h / 20 °C / Inert atmosphere

1.2: Dowex-H⁺ / 0.08 h / Inert atmosphere

2.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

With methanol; camphor-10-sulfonic acid; sodium methylate; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm201571p

upstream raw materials:

benzyl bromide

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

benzaldehyde dimethyl acetal

ethyl 1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-benzyl-4,6-O-phenylboronate-1-thio-β-D-glucopyranoside

Methanesulfonic acid (2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-ethylsulfanyl-2-methanesulfonyloxymethyl-tetrahydro-pyran-3-yl ester