phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside
• CAS No.: 241490-69-7
• Molecular Formula: C₂₂H₂₇NO₄S
• Molecular Weight: 401.527
• Mol file: 241490-69-7.mol

Synonyms:phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Chemical Property of phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

There total 2 articles about phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-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: 82.0%

acetic anhydride (108-24-7) + phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside (241490-67-5) → phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside (241490-69-7)

Guidance literature:

With pyridine; In chloroform; for 6h; Heating;

DOI:10.1021/jo990403l

Reference yield:

O-benzyl phenyl-2,6-dideoxy-1-thio-α,β-erythro-hexopyranosid-3-ulose oxime → phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside (241490-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cerium trichloride / tetrahydrofuran; diethyl ether / -78 °C

1.2: 24 percent / tetrahydrofuran; diethyl ether / -78 - -50 °C

2.1: 82 percent / pyridine / CHCl₃ / 6 h / Heating

With pyridine; cerium(III) chloride; In tetrahydrofuran; diethyl ether; chloroform; 1.1: Substitution / 1.2: Methylation / 2.1: Acetylation;

DOI:10.1021/jo990403l

Reference yield:

phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside (241490-69-7) → methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside (241490-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triflic acid; N-iodosuccinimide / 1,2-dichloro-ethane; diethyl ether

2: 92 percent / NaOCH₃ / methanol / 15 h

3: 68 percent Turnov_. / silver triflate; s-collidine; molecular sieves 4A / benzene

With 2,4,6-trimethyl-pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; diethyl ether; 1,2-dichloro-ethane; benzene; 1: glycosylation; coupling / 2: Deacetylation / 3: glycosylation; coupling;

DOI:10.1021/jo990403l

upstream raw materials:

acetic anhydride

phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Downstream raw materials:

methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside

methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside

Acetic acid (2S,3R,4R,6S)-4-benzyloxyamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

methyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside