(S)-N-carbobenzyloxycleonin

Base Information

• Chemical Name: (S)-N-carbobenzyloxycleonin
• CAS No.: 377090-75-0
• Molecular Formula: C₁₃H₁₅NO₅
• Molecular Weight: 265.266
• Mol file: 377090-75-0.mol

Synonyms:(S)-N-carbobenzyloxycleonin

Chemical Property of (S)-N-carbobenzyloxycleonin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-carbobenzyloxycleonin

There total 5 articles about (S)-N-carbobenzyloxycleonin 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: 75.0%

1-(1-(benzyloxycarbonylamino)-2-hydroxyethyl)-1-hydroxycyclopropane (377090-74-9) → (S)-N-carbobenzyloxycleonin (377090-75-0)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/ol016477c

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (S)-N-carbobenzyloxycleonin (377090-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / BF₃*Et₂O / acetone

2: 64 percent / Ti(i-PrO)4 / diethyl ether / 20 °C

3: 85 percent / PPTS / methanol / 8 h / 20 °C

4: 75 percent / PDC / dimethylformamide / 12 h / 20 °C

With titanium(IV) isopropylate; dipyridinium dichromate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; In methanol; diethyl ether; N,N-dimethyl-formamide; acetone; 2: Kulinkovich cyclopropanation;

DOI:10.1021/ol016477c

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-N-carbobenzyloxycleonin (377090-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / H₂O / 3 h / 20 °C

2: 95 percent / BF₃*Et₂O / acetone

3: 64 percent / Ti(i-PrO)4 / diethyl ether / 20 °C

4: 85 percent / PPTS / methanol / 8 h / 20 °C

5: 75 percent / PDC / dimethylformamide / 12 h / 20 °C

With titanium(IV) isopropylate; dipyridinium dichromate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; 3: Kulinkovich cyclopropanation;

DOI:10.1021/ol016477c

upstream raw materials:

1-(1-(benzyloxycarbonylamino)-2-hydroxyethyl)-1-hydroxycyclopropane

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

benzyl chloroformate

3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Downstream raw materials:

(S)-cleonin