5a-Carba-D-glycero-β-D-ido-heptopyranose

Base Information

• Chemical Name: 5a-Carba-D-glycero-β-D-ido-heptopyranose
• CAS No.: 345341-29-9
• Molecular Formula: C₈H₁₆O₆
• Molecular Weight: 208.211
• Mol file: 345341-29-9.mol

Synonyms:

Chemical Property of 5a-Carba-D-glycero-β-D-ido-heptopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5a-Carba-D-glycero-β-D-ido-heptopyranose

There total 6 articles about 5a-Carba-D-glycero-β-D-ido-heptopyranose 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:

(1S,3R,4R,5R,6S,9S)-3,9-Diacetoxy-4,5-isopropylidenedioxy-7-oxabicyclo[4.3.0]nonan-8-one (345341-27-7) → 5a-Carba-D-glycero-β-D-ido-heptopyranose (345341-29-9)

Guidance literature:

With calcium borohydride; In ethanol; at -10 - 20 ℃;

Reference yield:

D-erythro-L-galacto-Octono-1,4-lactone (56570-93-5) → 5a-Carba-D-glycero-β-D-ido-heptopyranose (345341-29-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. HBr / acetic acid / 0.5 h / 20 °C

1.2: aq. HBr / acetic acid; methanol / 20 °C

2.1: 3.6 g / H(+) / 48 h / Heating

3.1: 87 percent / pyridine / 1.5 h / 20 °C

4.1: 54 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

5.1: 73 percent / Bu₃SnH; AIBN / ethyl acetate / 2 h / Heating

6.1: 0.173 g / Ca(BH₄)2 / ethanol / -10 - 20 °C

With pyridine; calcium borohydride; 2,2'-azobis(isobutyronitrile); hydrogen bromide; tri-n-butyl-tin hydride; hydrogen cation; triethylamine; In ethanol; dichloromethane; acetic acid; ethyl acetate;

Reference yield:

8-Bromo-8-deoxy-5,6-O-isopropylidene-D-erythro-L-galacto-octono-1,4-lactone (345341-23-3) → 5a-Carba-D-glycero-β-D-ido-heptopyranose (345341-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / pyridine / 1.5 h / 20 °C

2: 54 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

3: 73 percent / Bu₃SnH; AIBN / ethyl acetate / 2 h / Heating

4: 0.173 g / Ca(BH₄)2 / ethanol / -10 - 20 °C

With pyridine; calcium borohydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In ethanol; dichloromethane; ethyl acetate;

upstream raw materials:

(1S,3R,4R,5R,6S,9S)-3,9-Diacetoxy-4,5-isopropylidenedioxy-7-oxabicyclo[4.3.0]nonan-8-one

D-erythro-L-galacto-Octono-1,4-lactone

8-Bromo-8-deoxy-D-erythro-L-galacto-octono-1,4-lactone

8-Bromo-8-deoxy-5,6-O-isopropylidene-D-erythro-L-galacto-octono-1,4-lactone