Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester
• CAS No.: 108470-01-5
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439
• Mol file: 108470-01-5.mol

Synonyms:Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

There total 12 articles about Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester 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: 90.0%

Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2,4-dimethyl-2-((E)-3-trityloxy-propenyl)-tetrahydro-furan-3-yl ester (120615-69-2) → Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (108470-01-5)

Guidance literature:

toluene-4-sulfonic acid; In methanol; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89819-7

Reference yield:

(E)-(4R,5R)-4-Benzyloxy-5-methoxymethoxy-2,4-dimethyl-hept-2-en-1-ol (108469-97-2) → Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (108470-01-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / mCPBA / CH₂Cl₂ / - 30 deg C, 7 h, - 20 deg C, 18 h,

2: 1.) DMSO, oxalyl chloride 2.) Et₃N / 1.) DMSO, oxalyl chloride, CH₂Cl₂, - 50 deg C, 15 min 2.) Et₃N, warm to room temp

3: 93 percent / benzene / 1 h / Ambient temperature

4: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

5: 100 percent / DIBAL-H / 1 h / -78 °C

6: 82 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

7: pyridine

8: 90 percent / TsOH / methanol / 1 h / Ambient temperature

With pyridine; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; toluene-4-sulfonic acid; In methanol; dichloromethane; chloroform; benzene;

DOI:10.1016/S0040-4020(01)89819-7

Reference yield:

(E)-3-[(2R,3S)-3-((1S,2R)-1-Benzyloxy-2-methoxymethoxy-1-methyl-butyl)-2-methyl-oxiranyl]-acrylic acid ethyl ester (108469-99-4) → Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (108470-01-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

2: 100 percent / DIBAL-H / 1 h / -78 °C

3: 82 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

4: pyridine

5: 90 percent / TsOH / methanol / 1 h / Ambient temperature

With pyridine; diisobutylaluminium hydride; trifluoroacetic acid; toluene-4-sulfonic acid; In methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4020(01)89819-7

upstream raw materials:

acetic anhydride

(E)-3-((2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-3-hydroxy-2,4-dimethyl-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

Acetic acid (2S,3S,4S,5R)-4-benzyloxy-5-ethyl-2,4-dimethyl-2-((E)-3-trityloxy-propenyl)-tetrahydro-furan-3-yl ester

(E)-(4R,5R)-4-Benzyloxy-5-methoxymethoxy-2,4-dimethyl-hept-2-en-1-ol

Downstream raw materials:

Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2R,3S)-3-hydroxymethyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3R)-3-hydroxymethyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester

aurovertin B

Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester