(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

Base Information

Chemical Name:(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol
CAS No.:164215-29-6
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

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Chemical Property of (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

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Technology Process of (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

There total 7 articles about (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-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: 78.0%

: 171189-78-9
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-4-trimethylsilanyl-but-3-yne-1,2-diol

: 164215-29-6
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

Guidance literature:: With potassium carbonate; at 23 ℃; for 8h;
DOI:10.1021/ja00136a008

Reference yield:

: 25636-49-1
3,3-dimethoxypentane

: 164215-29-6
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / p-TsOH / tetrahydrofuran / 4 h / Heating

2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, a) 0 deg C, 15 min, b) 23 deg C, 3 h

3: tetrahydrofuran / 0.17 h / -78 °C

4: 84 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, EtOH, -78 deg C, 2.5 h, 2.) CH₂Cl₂, EtOH, from -78 to 23 deg C

6: NaBH₄ / methanol / 2 h / 0 - 23 °C

7: 78 percent / methanolic K₂CO₃ / 8 h / 23 °C

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/ja00136a008

Reference yield:

: 164215-26-3
(R)-2-Benzyloxy-2-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-acetamide

: 164215-29-6
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 0.17 h / -78 °C

2: 84 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, EtOH, -78 deg C, 2.5 h, 2.) CH₂Cl₂, EtOH, from -78 to 23 deg C

4: NaBH₄ / methanol / 2 h / 0 - 23 °C

5: 78 percent / methanolic K₂CO₃ / 8 h / 23 °C

With sodium tetrahydroborate; potassium carbonate; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/ja00136a008