4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

Base Information

Chemical Name:4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose
CAS No.:153693-39-1
Molecular Formula:C₂₀H₂₈O₇S
Molecular Weight:412.504
Hs Code.:

Synonyms:4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

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Chemical Property of 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

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Technology Process of 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

There total 6 articles about 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose 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:

: 3282-30-2
pivaloyl chloride

: 153693-39-1
4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / pyridine / 6 h / 60 °C

2: 92 percent / mCPBA / CH₂Cl₂ / 0.83 h / -78 - 0 °C

With pyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/ja00084a018

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 153693-39-1
4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 10 h / 25 °C

2: AcOH, H₂O / tetrahydrofuran / 48 h / 70 °C

3: 1.) 4-A sieves, Bu₂SnO / 1.) DMF, 80 deg C, 5 h, 2.) DMF, 80 deg C, 6 h

4: 82 percent / pyridine / 6 h / 60 °C

5: 92 percent / mCPBA / CH₂Cl₂ / 0.83 h / -78 - 0 °C

With pyridine; 4 A molecular sieve; water; di(n-butyl)tin oxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00084a018

Reference yield:

: 1214-98-8,105026-40-2,127061-11-4,131724-82-8
phenyl 1-thio-α-L-rhamnopyranose

: 153693-39-1
4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: ZnCl₂, 85percent H₃PO₄ / 24 h / 25 °C

2: pyridine / 10 h / 25 °C

3: AcOH, H₂O / tetrahydrofuran / 48 h / 70 °C

4: 1.) 4-A sieves, Bu₂SnO / 1.) DMF, 80 deg C, 5 h, 2.) DMF, 80 deg C, 6 h

5: 82 percent / pyridine / 6 h / 60 °C

6: 92 percent / mCPBA / CH₂Cl₂ / 0.83 h / -78 - 0 °C

With pyridine; phosphoric acid; 4 A molecular sieve; water; di(n-butyl)tin oxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00084a018