ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside
• CAS No.: 182167-81-3
• Molecular Formula: C₂₂H₂₄O₅S
• Molecular Weight: 400.496
• Mol file: 182167-81-3.mol

Synonyms:ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside

Chemical Property of ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside

There total 13 articles about ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside 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:

C26H26N2O6S2 → ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside (182167-81-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 0.333333h; Reflux;

DOI:10.1039/b823428k

Reference yield:

benzoyl chloride (98-88-4) → ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside (182167-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / 1 h / Ambient temperature

2: 84 percent / H₂SO₄ / 0.75 h / 0 °C

3: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; sulfuric acid; tin(IV) chloride; In dichloromethane;

DOI:10.1080/07328309608005684

Reference yield:

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (112612-45-0) → ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside (182167-81-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 75 percent / LiAlH₄ / diethyl ether / 2 h / Heating

3: 80 percent / 50percent aq. AcOH / 1 h / 60 °C

4: pyridine, SOCl₂ / ethyl acetate / 0.5 h / 0 °C

5: aq. NaIO₄, RuCl₃ / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

7: 93 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

8: 95 percent / pyridine / 1 h / Ambient temperature

9: 84 percent / H₂SO₄ / 0.75 h / 0 °C

10: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; thionyl chloride; sulfuric acid; water; tin(IV) chloride; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005684

upstream raw materials:

1-O-Acetyl 2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranose

ethanethiol

Methyl 2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranoside

benzoyl chloride

Downstream raw materials:

Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside