(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

Base Information

Chemical Name:(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane
CAS No.:864658-68-4
Molecular Formula:C₂₇H₄₀O₄
Molecular Weight:428.612
Hs Code.:

Synonyms:(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

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Chemical Property of (R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

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Technology Process of (R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

There total 11 articles about (R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane 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:

: 864658-67-3
(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentanol

: 113826-06-5,6746-81-2
(R)-glycidyl tosylate

: (S)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

: 864658-68-4
(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

Guidance literature:: (1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentanol; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;

(R)-glycidyl tosylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 6h; Title compound not separated from byproducts;
DOI:10.1016/j.tetlet.2005.05.150

Reference yield:

: 241147-40-0,704910-24-7
(1R,2R)-2-Methoxymethoxy-cyclopentanol

: 864658-68-4
(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

Guidance literature:: Multi-step reaction with 6 steps

1.1: diethyl azodicarboxylate; Ph₃P / toluene / 1 h / 80 °C

1.2: K₂CO₃; MeOH / 1 h / 40 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2.2: tetrahydrofuran; dimethylformamide / 6 h / 20 °C

3.1: 91 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.25 h / -78 °C

4.1: 88 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 24 h / 20 °C

5.1: 87 percent / AcCl; MeOH / CH₂Cl₂ / 3 h / 40 °C

6.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

6.2: tetrahydrofuran; dimethylformamide / 6 h / 20 °C

With methanol; n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; acetyl chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu inversion;
DOI:10.1016/j.tetlet.2005.05.150

Reference yield:

: 864658-75-3,704910-24-7
(1S,2R)-2-Methoxymethoxy-cyclopentanol

: 864658-68-4
(R)-2-[(1R,2S)-2-((R)-2-Benzyloxy-dodec-4-ynyloxy)-cyclopentyloxymethyl]-oxirane

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

1.2: tetrahydrofuran; dimethylformamide / 6 h / 20 °C

2.1: 91 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.25 h / -78 °C

3.1: 88 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 24 h / 20 °C

4.1: 87 percent / AcCl; MeOH / CH₂Cl₂ / 3 h / 40 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

5.2: tetrahydrofuran; dimethylformamide / 6 h / 20 °C

With methanol; n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; acetyl chloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.05.150