(1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate

Base Information

• Chemical Name: (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate
• CAS No.: 864858-33-3
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 864858-33-3.mol

Synonyms:(1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate

Chemical Property of (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate

There total 7 articles about (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate 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: 91.0%

(1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol (864858-30-0) + acetic anhydride (108-24-7) → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate (864858-33-3)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1021/jo051047b

Reference yield:

5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose (864858-18-4) → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate (864858-33-3)

Guidance literature:

Multi-step reaction with 6 steps

1: DBU / acetonitrile / 80 °C

2: 82 percent / ZnEt₂ / toluene / 0 °C

3: HCl / dioxane / 0 °C

4: CrO₃; acetic anhydride; pyridine / CH₂Cl₂ / 0 °C

5: NaBH₄ / ethanol

6: pyridine

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; diethylzinc; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; ethanol; dichloromethane; toluene; acetonitrile; 2: Simmons-Smith reaction;

DOI:10.1081/NCN-200059796

Reference yield:

[(3aS,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzyl ether (864858-21-9) → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate (864858-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / ZnEt₂ / toluene / 0 °C

2: HCl / dioxane / 0 °C

3: CrO₃; acetic anhydride; pyridine / CH₂Cl₂ / 0 °C

4: NaBH₄ / ethanol

5: pyridine

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; diethylzinc; acetic anhydride; In 1,4-dioxane; ethanol; dichloromethane; toluene; 1: Simmons-Smith reaction;

DOI:10.1081/NCN-200059796

upstream raw materials:

(1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol

acetic anhydride

[(3aS,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzyl ether

(1S,3S,4S,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol