((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

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Chemical Name:((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester
CAS No.:700361-01-9
Molecular Formula:C₂₀H₂₉NO₄
Molecular Weight:347.455
Hs Code.:

Synonyms:((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

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Chemical Property of ((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

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Technology Process of ((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

There total 10 articles about ((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl 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: 56.0%

: 1826-67-1
vinyl magnesium bromide

: 700360-99-2
[(R)-1-((S)-1-Benzyloxy-2-oxo-ethyl)-but-3-enyl]-carbamic acid tert-butyl ester

: ((1R,2S,3R)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

: 700361-01-9
((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1016/j.tetlet.2004.03.051

Reference yield:

: 54594-06-8
D-allylglycine

: 700361-01-9
((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: methanol / 2 h / Heating

2.1: Et₃N / 18 h / 20 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

4.1: NaBH₄ / methanol / 0.5 h / 0 °C

4.2: dioxane / 18 h / 20 °C

5.1: diethyl ether / 6 h / -78 - -45 °C

6.1: NaBH₄ / methanol / 0.5 h / 0 °C

7.1: 90 percent / NaH / dimethylformamide / 1 h / 0 °C

8.1: 67 percent / CAN; NaHCO₃ / acetonitrile; H₂O / 0.5 h / 20 °C

9.1: MeOTf / acetonitrile / 0.42 h / 20 °C

9.2: NaBH₄ / methanol / 0.17 h / 0 °C

9.3: 83 percent / CuCl₂*2H₂O; CuO / acetonitrile; H₂O / 0.25 h / 20 °C

10.1: 56 percent / tetrahydrofuran / 4 h / -78 °C

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; sodium hydride; sodium hydrogencarbonate; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; 10.1: Grignard addition;
DOI:10.1016/j.tetlet.2004.03.051

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 700361-01-9
((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaBH₄ / methanol / 0.5 h / 0 °C

1.2: dioxane / 18 h / 20 °C

2.1: diethyl ether / 6 h / -78 - -45 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 90 percent / NaH / dimethylformamide / 1 h / 0 °C

5.1: 67 percent / CAN; NaHCO₃ / acetonitrile; H₂O / 0.5 h / 20 °C

6.1: MeOTf / acetonitrile / 0.42 h / 20 °C

6.2: NaBH₄ / methanol / 0.17 h / 0 °C

6.3: 83 percent / CuCl₂*2H₂O; CuO / acetonitrile; H₂O / 0.25 h / 20 °C

7.1: 56 percent / tetrahydrofuran / 4 h / -78 °C

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; sodium hydride; sodium hydrogencarbonate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; 7.1: Grignard addition;
DOI:10.1016/j.tetlet.2004.03.051