(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

Base Information

Chemical Name:(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran
CAS No.:123493-08-3
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

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Chemical Property of (2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

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Technology Process of (2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

There total 11 articles about (2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran 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: 65.0%

: 917-54-4
methyllithium

: 115133-12-5
(1S,2S,4R,6S)-7-benzoyl-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one

: 123493-08-3
(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

Guidance literature:: With ammonium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;
DOI:10.1016/0040-4020(89)80126-7

Reference yield:

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

: 123493-08-3
(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 7 steps

1: O₃; dimethylsulfide / CH₂Cl₂ / 21.16 h / -78 - 20 °C

2: 68 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene / CH₂Cl₂ / 1.17 h / Heating

3: 85 percent / 1.) diisopropylamine, 1.60 M n-butyllithium. / 1.) tetrahydrofuran/hexan, 0 deg C, 10 min; 2.) tetrahydrofuran/hexan, RT, 10 h

4: 98 percent / Dowex 50X₈-100 / methanol / 5 h / Ambient temperature

5: 78 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.33 h / 0 °C

6: 98 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Heating

7: 65 percent / aq. ammonium chloride / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; dimethylsulfide; Dowex 50x8-100; ammonium chloride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1016/0040-4020(89)80126-7

Reference yield:

: 101977-77-9
<3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

: 123493-08-3
(2S,3S,4S,6R)-3-acetyl-4-benzoylamino-6-methoxy-2-(methyl)tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 7 steps

1: O₃; dimethylsulfide / CH₂Cl₂ / 21.16 h / -78 - 20 °C

2: 68 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene / CH₂Cl₂ / 1.17 h / Heating

3: 85 percent / 1.) diisopropylamine, 1.60 M n-butyllithium. / 1.) tetrahydrofuran/hexan, 0 deg C, 10 min; 2.) tetrahydrofuran/hexan, RT, 10 h

4: 98 percent / Dowex 50X₈-100 / methanol / 5 h / Ambient temperature

5: 78 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.33 h / 0 °C

6: 98 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Heating

7: 65 percent / aq. ammonium chloride / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; dimethylsulfide; Dowex 50x8-100; ammonium chloride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1016/0040-4020(89)80126-7