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

Base Information

• Chemical Name: (-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol
• CAS No.: 945915-30-0
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 945915-30-0.mol

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

Chemical Property of (-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol

There total 1 articles about (-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-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: 74.0%

(benzyloxymethyl)tributylstannane (66222-28-4) + (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → (-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol (945915-30-0)

Guidance literature:

(benzyloxymethyl)tributylstannane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one; In tetrahydrofuran; at -78 ℃; for 1.33333h; Further stages.;

DOI:10.1016/j.tet.2007.04.094

Reference yield: 72.0%

(-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol (945915-30-0) + benzoyl chloride (98-88-4) → (-)-(1S,4R,5R)-1-benzoyloxy-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopentene (945915-31-1)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.tet.2007.04.094

Reference yield:

(-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol (945915-30-0) → (-)-9-[(1R,2S,5R)-2-benzyloxy-4-[(benzyloxy)methyl]-5-methoxymethoxy-cyclopent-3-en-1-yl]-6-aminopurine (945915-41-3)

Guidance literature:

Multi-step reaction with 8 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

8.1: 60 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 3 h / 60 °C

With pyridine; dmap; sodium hydroxide; ammonium cerium(IV) nitrate; 18-crown-6 ether; sodium hydride; potassium carbonate; acetic acid; p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.04.094

upstream raw materials:

(benzyloxymethyl)tributylstannane

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

Downstream raw materials:

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

(-)-(1R,4S,5S)-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopenten-1-ol

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

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