3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol

Base Information

• Chemical Name: 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol
• CAS No.: 560088-49-5
• Molecular Formula: C₂₃H₂₈O₉
• Molecular Weight: 448.47

Synonyms:3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol

Chemical Property of 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

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Technology Process of 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol

There total 1 articles about 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol 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:

1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol (104006-65-7) + 3,4-di-O-acetyl-2,6-dideoxy-1-phenylthio-α-L-arabino-pyranoside (135197-78-3) → 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol (560088-49-5)

Guidance literature:

1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol; 3,4-di-O-acetyl-2,6-dideoxy-1-phenylthio-α-L-arabino-pyranoside; With 4 A molecular sieve; Selectfluor; In acetonitrile; at 0 ℃;

With Amberlyst A-21; In acetonitrile;

With trimethylammoniomethyl-polymer borohydride; In isopropyl alcohol; at 20 ℃;

DOI:10.1002/anie.200390307

Reference yield: 46.0%

testosterone (58-22-0) + 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol (560088-49-5) → 17-O-[4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-(1->4)-(3-O-benzoyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)]testosterone + 17-O-[4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-(1->4)-(3-O-benzoyl-2,6-dideoxy-β-L-arabino-hexopyranosyl]testosterone

Guidance literature:

polymer-bound PPh₂HBr; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200400069

Reference yield:

testosterone (58-22-0) + 3-O-benzoyl-2,6-dideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-L-arabino-hex-1-enitol (560088-49-5) → benzoic acid 3-(4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-(10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yloxy)-2-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:

With polymer-bound sulfonic acid;

DOI:10.1002/anie.200390307

upstream raw materials:

1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol

3,4-di-O-acetyl-2,6-dideoxy-1-phenylthio-α-L-arabino-pyranoside

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