Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester
CAS No.:221182-36-1
Molecular Formula:C₁₇H₂₂FNO₅
Molecular Weight:339.364
Hs Code.:

Synonyms:Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester 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:

: Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester

: 221182-36-1
Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 221182-36-1
Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaHCO₃, H₂O / dioxane / 2 h / 23 °C

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 to 23 deg C, 6 h

3: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

4: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

5: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

6: 1.) NBS, H₂O, 2.) DAST / 1.) acetone, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min

With dmap; N-Bromosuccinimide; dimethylsulfide; boron trifluoride diethyl etherate; water; sodium hydrogencarbonate; ozone; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In 1,4-dioxane; dichloromethane;
DOI:10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5

Reference yield:

: 213681-52-8
(2S,3S,4S)-4-Benzyloxyamino-4-methyl-2-triisopropylsilanyloxy-hept-6-en-3-ol

: 221182-36-1
Acetic acid (2S,3S,4S)-4-benzyloxycarbonylamino-6-fluoro-2,4-dimethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / NaH / tetrahydrofuran / 3 h / 0 - 23 °C

2: LiAlH₄ / diethyl ether / 18 h / Heating

3: NaHCO₃, H₂O / dioxane / 2 h / 23 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 to 23 deg C, 6 h

5: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

6: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

7: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

8: 1.) NBS, H₂O, 2.) DAST / 1.) acetone, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min

With dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; dimethylsulfide; boron trifluoride diethyl etherate; water; sodium hydride; sodium hydrogencarbonate; ozone; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5