4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol

Base Information

• Chemical Name: 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol
• CAS No.: 52945-57-0
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 52945-57-0.mol

Synonyms:4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol

Chemical Property of 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol

There total 1 articles about 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-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: 50.0%

4-N-benzoylcytosine (26661-13-2) + methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside (23339-17-5) → 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol (52945-57-0) + N4-Benzoyl-1-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-glucopyranosyl)cytosin (145593-79-9) + N4-Benzoyl-1-(4',6'-di-O-acetyl-2',3'-dideoxy-β-D-glucopyranosyl)cytosin (145593-78-8)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In acetonitrile; 1) r.t., 30 min, 2) 45 - 50 deg C, 2 h;

DOI:10.1002/hlca.19920750503

Reference yield: 88.0%

N-benzoyl-1-methoxy-1-(1-naphthyl)-methylamine + 4,6-di-O-acetyl-3-deoxygalactal (52945-57-0,60873-27-0,115181-97-0) → (4S,6R,4aS,8aR)-acetic acid 6-acetoxy-4-naphthalen-1-yl-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester (1332628-33-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol2019604

Reference yield: 83.0%

N-benzoyl-1-methoxy-1-(p-methylphenyl)-methylamine + 4,6-di-O-acetyl-3-deoxygalactal (52945-57-0,60873-27-0,115181-97-0) → (4S,6R,4aS,8aR)-acetic acid 6-acetoxy-2-phenyl-4-p-tolyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-7-ylmethyl ester (1332628-34-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol2019604

upstream raw materials:

4-N-benzoylcytosine

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside

Downstream raw materials:

Acetic acid (1R,3R,4S,6S)-3-acetoxymethyl-7-oxo-8-(toluene-4-sulfonyl)-2-oxa-8-aza-bicyclo[4.2.0]oct-4-yl ester

Acetic acid (1S,3R,4S,6R)-3-acetoxymethyl-7-oxo-8-(toluene-4-sulfonyl)-2-oxa-8-aza-bicyclo[4.2.0]oct-4-yl ester

(4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-4-naphthalen-1-yl-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester

(4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-4-(3-nitro-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester