rac-Carba-β-arabinofuranose

Base Information

• Chemical Name: rac-Carba-β-arabinofuranose
• CAS No.: 119944-85-3
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• Mol file: 119944-85-3.mol

Synonyms:

Chemical Property of rac-Carba-β-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-Carba-β-arabinofuranose

There total 7 articles about rac-Carba-β-arabinofuranose 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: 83.0%

rac-1,2,3,5-Tetra-O-acetylcarba-β-arabinofuranose → rac-Carba-β-arabinofuranose (105265-95-0,113299-30-2,113299-31-3,113299-32-4,115509-85-8,118013-55-1,118013-56-2,119905-80-5,119905-83-8,119944-85-3,144938-80-7)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00121a046

Reference yield:

methyl (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-carboxylate (105265-92-7) → rac-Carba-β-arabinofuranose (105265-95-0,113299-30-2,113299-31-3,113299-32-4,115509-85-8,118013-55-1,118013-56-2,119905-80-5,119905-83-8,119944-85-3,144938-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 2 h / -78 °C

2: 1.) borane-THF complex, 2.) 3M NaOH, 35percent H₂O₂ / 1.) THF, 0 deg C, 2.5 h, 2.) water, RT, 2 h

3: 90percent CH₃COOH / 3 h / Heating

With sodium hydroxide; borane-THF; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; In dichloromethane; toluene;

DOI:10.1021/jo00386a011

Reference yield:

(3aS,6aS)-4-Acetoxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5,5-dicarboxylic acid dimethyl ester (105265-91-6,105368-86-3) → rac-Carba-β-arabinofuranose (105265-95-0,113299-30-2,113299-31-3,113299-32-4,115509-85-8,118013-55-1,118013-56-2,119905-80-5,119905-83-8,119944-85-3,144938-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaCl / dimethylsulfoxide; H₂O / 10 h / 110 - 160 °C

2: 67 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 2 h / -78 °C

3: 1.) borane-THF complex, 2.) 3M NaOH, 35percent H₂O₂ / 1.) THF, 0 deg C, 2.5 h, 2.) water, RT, 2 h

4: 90percent CH₃COOH / 3 h / Heating

With sodium hydroxide; borane-THF; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; sodium chloride; In dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jo00386a011

upstream raw materials:

(3aS,4S,6R,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one

(3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

(3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol