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

Base Information

Chemical Name:(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol
CAS No.:945915-39-9
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

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

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Chemical Property of (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

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Technology Process of (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

There total 9 articles about (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol 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: 60.0%

: 945915-38-8
(-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-2-cyclopentene-4,5-diol

: 149-73-5
trimethyl orthoformate

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

Guidance literature:: (-)-(1R,4S,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-2-cyclopentene-4,5-diol; trimethyl orthoformate; With ammonium cerium(IV) nitrate; In dichloromethane; at 20 ℃; for 3h;

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h; Further stages.;
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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 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:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 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