[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester
CAS No.:84787-52-0
Molecular Formula:C₁₆H₂₁NO₅
Molecular Weight:307.346
Hs Code.:

Synonyms:[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

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Chemical Property of [(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

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Technology Process of [(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

There total 2 articles about [(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl 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:

: 77856-52-1
(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid

: 84787-52-0
[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH₄

2: Ac₂O / pyridine

3: 77 percent / LDA / tetrahydrofuran / 1 h / -78 °C

With sodium tetrahydroborate; acetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; pyridine;
DOI:10.1021/ja00344a044

Reference yield:

: (S)-3-Benzyloxycarbonylamino-5-methoxy-pentanoic acid

: 84787-52-0
[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Ac₂O / pyridine

2: 77 percent / LDA / tetrahydrofuran / 1 h / -78 °C

With acetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; pyridine;
DOI:10.1021/ja00344a044

Reference yield:

: 84787-52-0
[(3R,4R)-3-(1-Hydroxy-1-methyl-ethyl)-2-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

: 92530-27-3
2-Diazo-4-[(2R,3R)-3-(1-methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent Turnov_. / hydrochloric acid

2: H₂, catalyst

3: Et₃N / diethyl ether / 2 h / 25 °C

4: t-BuMgCl / diethyl ether / 12 h / 25 °C

5: 1percent AcOH / methanol / 24 h / 25 °C

6: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

7: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

8: TsN₃, Et₃N / acetonitrile / 12 h / 25 °C

With chromium(VI) oxide; hydrogenchloride; 4-toluenesulfonyl azide; tert-butylmagnesium chloride; hydrogen; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; In pyridine; methanol; diethyl ether; acetonitrile;
DOI:10.1021/ja00344a044