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

Base Information

• Chemical Name: (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol
• CAS No.: 864858-30-0
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 864858-30-0.mol

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

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

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]hexan-4-ol

There total 6 articles about (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-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:

(1S,3S,5R)-1-Benzyloxymethyl-3-methoxy-2-oxa-bicyclo[3.1.0]hexan-4-one → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol (864858-30-0)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃;

DOI:10.1021/jo051047b

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]hexan-4-ol (864858-30-0)

Guidance literature:

Multi-step reaction with 4 steps

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

2: HCl / dioxane / 0 °C

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

4: NaBH₄ / ethanol

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

Reference yield:

[(3aS,4aS,5aS,5bS)-2,2-dimethyltetrahydro-4aH-cyclopropa[4,5]furo[2,3-d][1,3]dioxol-4a-yl]methyl benzyl ether (864858-24-2) → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol (864858-30-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl / dioxane / 0 °C

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

3: NaBH₄ / ethanol

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; acetic anhydride; In 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1081/NCN-200059796

upstream raw materials:

[(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

[(3aS,4aS,5aS,5bS)-2,2-dimethyltetrahydro-4aH-cyclopropa[4,5]furo[2,3-d][1,3]dioxol-4a-yl]methyl benzyl ether

5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose

Downstream raw materials:

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