(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

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Chemical Name:(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol
CAS No.:696598-54-6
Molecular Formula:C₁₇H₂₆O₄
Molecular Weight:294.391
Hs Code.:

Synonyms:(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

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Chemical Property of (1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

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Technology Process of (1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

There total 6 articles about (1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol 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: 94.0%

: 696598-49-9
2-{(1S,2S,4S)-4-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylcyclobutyl}-2-propanolan-1-ol

: 696598-54-6
(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

Guidance literature:: With trifluoroacetic acid; In methanol; water; at 20 ℃;
DOI:10.1021/ol0497032

Reference yield:

: 84077-32-7
(-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone

: 696598-54-6
(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / acetonitrile / 7.5 h / -15 °C / UV-irradiation

2.1: 69 percent / Zn / ethanol; H₂O / 0.33 h / 105 °C / microwave irradiation

3.1: 86 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 20 °C

4.1: 91 percent / p-TsOH / 12 h / 20 °C

5.1: Hg(OAc)2 / H₂O; tetrahydrofuran / 2.5 h / 20 °C

5.2: 92 percent / NaOH; NaBH₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

6.1: NaH / tetrahydrofuran / 2 h / cooling

6.2: 79 percent / tetrahydrofuran

7.1: 94 percent / CF₃CO₂H / methanol; H₂O / 20 °C

With mercury(II) diacetate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1021/ol0497032

Reference yield:

: 500777-28-6
(1R,4S,5S)-5-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one

: 696598-54-6
(1S)-1-[(1S,2S,3S)-3-(benzyloxy)-2-(1-hydroxy-1-methylethyl)-1-methylcyclobutyl]ethane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 20 °C

2.1: 91 percent / p-TsOH / 12 h / 20 °C

3.1: Hg(OAc)2 / H₂O; tetrahydrofuran / 2.5 h / 20 °C

3.2: 92 percent / NaOH; NaBH₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

4.1: NaH / tetrahydrofuran / 2 h / cooling

4.2: 79 percent / tetrahydrofuran

5.1: 94 percent / CF₃CO₂H / methanol; H₂O / 20 °C

With mercury(II) diacetate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; water;
DOI:10.1021/ol0497032