5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal

Base Information

• Chemical Name: 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal
• CAS No.: 143426-05-5
• Molecular Formula: C₃₃H₄₀O₇
• Molecular Weight: 548.676
• Mol file: 143426-05-5.mol

Synonyms:

Chemical Property of 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal

There total 1 articles about 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal 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:

Propiolaldehyde diethyl acetal (10160-87-9) + 2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal (143426-05-5)

Guidance literature:

With ethylmagnesium bromide; Yield given. Multistep reaction; 1) THF, 60 deg C, 1 h, 2) THF, 60 deg C, 10 h, then rt, 24 h;

Reference yield: 66.0%

pivaloyl chloride (3282-30-2) + 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal (143426-05-5) → 5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-8-O-pivaloyl-D-ido-octose Diethyl Acetal (143426-06-6)

Guidance literature:

With pyridine; for 18h; Ambient temperature;

Reference yield:

5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal (143426-05-5) → 3(5)-(2',3'-Di-O-benzyl-β-D-xylofuranosyl)pyrazole (143426-09-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / pyridine / 18 h / Ambient temperature

2: 80 percent / p-TsCl, pyridine / 5 h / 80 °C

3: 1) aq. HCl, glacial acetic acid, 2) hydrazine hydrate, acetic acid / 1) rt, 0.5 h, 2) reflux, 2 h

4: 80 percent / NaOMe / methanol / 48 h / Ambient temperature

With pyridine; hydrogenchloride; sodium methylate; hydrazine hydrate; acetic acid; p-toluenesulfonyl chloride; In methanol;

upstream raw materials:

Propiolaldehyde diethyl acetal

2,3,4-tri-O-benzyl-D-xylopyranose

Downstream raw materials:

5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-8-O-pivaloyl-D-ido-octose Diethyl Acetal

3(5)-(2',3'-Di-O-benzyl-β-D-xylofuranosyl)pyrazole

3(5)-(2',3'-Di-O-benzyl-5'-O-pivaloyl-β-D-xylofuranosyl)pyrazole

1-(2,3-Di-O-benzyl-5-O-pivaloyl-β-D-xylofuranosyl)-3,3-diethoxyprop-1-yne

Refernces