(R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol

Base Information

• Chemical Name: (R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol
• CAS No.: 130740-50-0
• Molecular Formula: C₂₅H₄₀O₆
• Molecular Weight: 436.589
• Mol file: 130740-50-0.mol

Synonyms:

Chemical Property of (R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol

There total 34 articles about (R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-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: 75.0%

(3E,7E)-(2S,5S,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undeca-3,7-dien-1-ol (130740-49-7) → (R)-2-[3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol (130740-50-0,130852-79-8)

Guidance literature:

With tert.-butylhydroperoxide; hexacarbonyl molybdenum; In benzene;

DOI:10.1016/S0040-4039(00)97606-8

Reference yield:

(2R,3S)-4-Benzyloxy-3-methyl-butane-1,2-diol (59005-41-3,78479-16-0,80184-02-7,81422-90-4,117112-55-7,130321-91-4) → (R)-2-[3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol (130740-50-0,130852-79-8)

Guidance literature:

Multi-step reaction with 17 steps

2: iPr₂NEt

3: LiAlH₄

4: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

6: MnO₂

8: LiAlH₄

9: KH

10: LDA / tetrahydrofuran / -78 deg C to 0 deg C

11: KH

12: LiAlH₄ / H₂O; trifluoroacetic acid

13: Swern oxidation

14: ZnCl₂ / diethyl ether

15: H₂ / Lindlar

16: 1. KH / 1. DME; 2. -78 deg C

17: 75 percent / Mo(CO)6, TBHP / benzene

With tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; oxalyl dichloride; hexacarbonyl molybdenum; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4039(00)97606-8

Reference yield:

(2R,3S)-4-Benzyloxy-3-methyl-butane-1,2-diol (59005-41-3,78479-16-0,80184-02-7,81422-90-4,117112-55-7,130321-91-4) → (R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol (130740-50-0,130852-79-8)

Guidance literature:

Multi-step reaction with 18 steps

2: iPr₂NEt

3: LiAlH₄

4: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

6: MnO₂

8: LiAlH₄

9: KH

10: LDA / tetrahydrofuran / -78 deg C to 0 deg C

11: KH

12: LiAlH₄ / H₂O; trifluoroacetic acid

13: Swern oxidation

14: ZnCl₂ / diethyl ether

15: H₂ / Lindlar

16: 1. KH / 1. DME; 2. -78 deg C

17: 75 percent / Mo(CO)6, TBHP / benzene

18: NaH₂Al(OCH₂CH₂OMe)2, (Red-Al) / benzene / 80 °C

With tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; oxalyl dichloride; hexacarbonyl molybdenum; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4039(00)97606-8

upstream raw materials:

(3E,7E)-(2S,5S,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undeca-3,7-dien-1-ol

(2R,3S)-4-Benzyloxy-3-methyl-butane-1,2-diol

2,2-Dimethyl-propionic acid (2R,3S)-4-benzyloxy-2-hydroxy-3-methyl-butyl ester

(2R,3S)-4-Benzyloxy-2-methoxymethoxy-3-methyl-butyraldehyde

Downstream raw materials:

(R)-2-[(2R,3S)-3-((E)-(1R,2S,5R,6S)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-oxiranyl]-propan-1-ol

(E)-(2S,4R,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol

(E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol