(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

Base Information

Chemical Name:(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene
CAS No.:945915-40-2
Molecular Formula:C₂₃H₂₅F₃O₇S
Molecular Weight:502.509
Hs Code.:

Synonyms:(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

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Chemical Property of (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

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Technology Process of (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

There total 10 articles about (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene 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: 97.0%

: 945915-39-9
(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

: 358-23-6
trifluoromethylsulfonic anhydride

: 945915-40-2
(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

Guidance literature:: With dmap; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.tet.2007.04.094

Reference yield:

: 945915-31-1
(-)-(1S,4R,5R)-1-benzoyloxy-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopentene

: 945915-40-2
(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 82 percent / p-benzoquinone / PdCl₂[CH₃CN]2 / tetrahydrofuran / 24 h / Heating

2.1: 90 percent / NaOH / methanol / 1.5 h / 20 °C

3.1: 88 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 0 - 20 °C

4.1: 93 percent / acetic acid / H₂O / 16 h / 50 °C

5.1: ceric ammonium nitrate / CH₂Cl₂ / 3 h / 20 °C

5.2: 60 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -78 °C

6.1: 97 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; sodium hydroxide; ammonium cerium(IV) nitrate; sodium hydride; acetic acid; p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.04.094

Reference yield:

: 945915-30-0
(-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol

: 945915-40-2
(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-5-(trifluoromethanesulfonyl)-2-cyclopentene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 72 percent / pyridine / 20 °C

2.1: 82 percent / p-benzoquinone / PdCl₂[CH₃CN]2 / tetrahydrofuran / 24 h / Heating

3.1: 90 percent / NaOH / methanol / 1.5 h / 20 °C

4.1: 88 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 0 - 20 °C

5.1: 93 percent / acetic acid / H₂O / 16 h / 50 °C

6.1: ceric ammonium nitrate / CH₂Cl₂ / 3 h / 20 °C

6.2: 60 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -78 °C

7.1: 97 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; dmap; sodium hydroxide; ammonium cerium(IV) nitrate; sodium hydride; acetic acid; p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.04.094