methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate

Base Information

• Chemical Name: methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate
• CAS No.: 129885-80-9
• Molecular Formula: C₁₃H₂₀O₆
• Molecular Weight: 272.298
• Mol file: 129885-80-9.mol

Synonyms:

Chemical Property of methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate

There total 1 articles about methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate 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:

norborn-5-en-2-one (694-98-4) → methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate (129885-80-9,144016-20-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 30percent H₂O₂, NaOH / diethyl ether; H₂O / 2 h / Ambient temperature

2: dimethylformamide / 16 h / Ambient temperature

3: pyridine, N,N-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

4: N-methylmorpholine-N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

5: 71.6 percent / TosOH / 1 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; osmium(VIII) oxide; dihydrogen peroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)81872-X

Reference yield:

methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate (129885-80-9,144016-20-6) → 1-O-acetyl-3,4-O-isopropylidene-6-O-trityl-β-DL-ribo-carbahex-2-ulofuranose

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / LiAlH₄ / diethyl ether / 1) r.t., 15 min, 2) reflux, 15 min

2: 87 percent / Ph₃P, Br, Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 1) NaBH₄ / 1) EtOH, 0 deg C, 15 min, 2) EtOH, r.t., 16 h

4: 30percent H₂O₂ / tetrahydrofuran / 16 h / Ambient temperature

5: 1) OsO₄, NaIO₄, 2) LiAlH₄ / 1) Et₂O, H₂O, r.t., 16 h, 2) Et₂O, a) r.t., 15 min, b) reflux, 15 min

6: 78.8 percent / pyridine, N,N-dimethylaminopyridine / CH₂Cl₂ / 4 h / Ambient temperature

7: PDC / CH₂Cl₂ / 16 h / Ambient temperature

8: 1) NaH / 1) DMSO, r.t., 30 min, 2)THF, r.t., 60 min

9: 71.2 percent / dimethylformamide / 16 h / 90 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; bromine; dihydrogen peroxide; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81872-X

Reference yield:

methyl 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-β-DL-ribo-carbahexofuranuronate (129885-80-9,144016-20-6) → 3,4-O-isopropylidene-6-O-trityl-β-DL-ribo-carbahex-2-ulofuranose

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / LiAlH₄ / diethyl ether / 1) r.t., 15 min, 2) reflux, 15 min

2: 87 percent / Ph₃P, Br, Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 1) NaBH₄ / 1) EtOH, 0 deg C, 15 min, 2) EtOH, r.t., 16 h

4: 30percent H₂O₂ / tetrahydrofuran / 16 h / Ambient temperature

5: 1) OsO₄, NaIO₄, 2) LiAlH₄ / 1) Et₂O, H₂O, r.t., 16 h, 2) Et₂O, a) r.t., 15 min, b) reflux, 15 min

6: 78.8 percent / pyridine, N,N-dimethylaminopyridine / CH₂Cl₂ / 4 h / Ambient temperature

7: PDC / CH₂Cl₂ / 16 h / Ambient temperature

8: 1) NaH / 1) DMSO, r.t., 30 min, 2)THF, r.t., 60 min

9: 50 mg / dimethylformamide / 16 h / Heating

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; bromine; dihydrogen peroxide; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81872-X

upstream raw materials:

norborn-5-en-2-one

Downstream raw materials:

2',3'-isopropylidine (+/-) aristeromycin

(+/-)-2α,3α-Isopropylidenedioxy-4β-(triphenylmethoxymethyl)cyclopentane-1β-ol

(+/-)-2α,3α-Isopropylidenedioxy-4β-(triphenylmethoxymethyl)cyclopentanone

Refernces