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

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester
• CAS No.: 120595-07-5
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423
• Mol file: 120595-07-5.mol

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

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

There total 13 articles about Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-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:

(E)-(4R,5R)-4-Benzyloxy-5-methoxymethoxy-2,4-dimethyl-hept-2-en-1-ol (108469-97-2) → Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (120595-07-5)

Guidance literature:

Multi-step reaction with 10 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

9: 99 percent / diethyl D-tartrate, Ti(OiPr)4, TBHP / CH₂Cl₂ / 12 h / -20 °C

10: oxalyl chloride,DMSO,Et₃N

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; 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:

[(2R,3S)-3-((1S,2R)-1-Benzyloxy-2-methoxymethoxy-1-methyl-butyl)-2-methyl-oxiranyl]-methanol (108469-98-3) → Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (120595-07-5)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 93 percent / benzene / 1 h / Ambient temperature

3: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

4: 100 percent / DIBAL-H / 1 h / -78 °C

5: 82 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

6: pyridine

7: 90 percent / TsOH / methanol / 1 h / Ambient temperature

8: 99 percent / diethyl D-tartrate, Ti(OiPr)4, TBHP / CH₂Cl₂ / 12 h / -20 °C

9: oxalyl chloride,DMSO,Et₃N

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; toluene-4-sulfonic acid; In methanol; dichloromethane; chloroform; benzene;

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

Reference yield:

(E)-(4R,5R)-4-Benzyloxy-5-hydroxy-2,4-dimethyl-hept-2-enoic acid methyl ester (108469-96-1) → Acetic acid (2S,3R,4S,5R)-4-benzyloxy-5-ethyl-2-((2S,3S)-3-formyl-oxiranyl)-2,4-dimethyl-tetrahydro-furan-3-yl ester (120595-07-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 88 percent / P₂O₅ / CHCl₃ / 0.5 h / Ambient temperature

2: 100 percent / DIBAL-H / tetrahydrofuran / 1.5 h / -78 °C

3: 90 percent / mCPBA / CH₂Cl₂ / - 30 deg C, 7 h, - 20 deg C, 18 h,

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

5: 93 percent / benzene / 1 h / Ambient temperature

6: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

7: 100 percent / DIBAL-H / 1 h / -78 °C

8: 82 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

9: pyridine

10: 90 percent / TsOH / methanol / 1 h / Ambient temperature

11: 99 percent / diethyl D-tartrate, Ti(OiPr)4, TBHP / CH₂Cl₂ / 12 h / -20 °C

12: oxalyl chloride,DMSO,Et₃N

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; benzene;

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

upstream raw materials:

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

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

(E)-(4R,5R)-4-Benzyloxy-5-hydroxy-2,4-dimethyl-hept-2-enoic acid methyl ester

[(2R,3S)-3-((1S,2R)-1-Benzyloxy-2-methoxymethoxy-1-methyl-butyl)-2-methyl-oxiranyl]-methanol

Downstream raw materials:

aurovertin B

2,6-dioxabicyclo<3.2.1>octane

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