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

Base Information

• Chemical Name: (3E,7E)-(2S,5S,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undeca-3,7-dien-1-ol
• CAS No.: 130740-49-7
• Molecular Formula: C₂₅H₄₀O₅
• Molecular Weight: 420.59
• Mol file: 130740-49-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (3E,7E)-(2S,5S,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undeca-3,7-dien-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:

(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) → (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)

Guidance literature:

Multi-step reaction with 16 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

With manganese(IV) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 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;

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

Reference yield:

(2R,3S)-4-Benzyloxy-2-methoxymethoxy-3-methyl-butan-1-ol → (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)

Guidance literature:

Multi-step reaction with 13 steps

1: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

3: MnO₂

5: LiAlH₄

6: KH

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

8: KH

9: LiAlH₄ / H₂O; trifluoroacetic acid

10: Swern oxidation

11: ZnCl₂ / diethyl ether

12: H₂ / Lindlar

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

With manganese(IV) oxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; trifluoroacetic acid;

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

Reference yield:

2,2-Dimethyl-propionic acid (2R,3S)-4-benzyloxy-2-hydroxy-3-methyl-butyl ester (95532-13-1) → (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)

Guidance literature:

Multi-step reaction with 15 steps

1: iPr₂NEt

2: LiAlH₄

3: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

5: MnO₂

7: LiAlH₄

8: KH

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

10: KH

11: LiAlH₄ / H₂O; trifluoroacetic acid

12: Swern oxidation

13: ZnCl₂ / diethyl ether

14: H₂ / Lindlar

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

With manganese(IV) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 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;

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

upstream raw materials:

methyllithium

trimethylstannylmethyl iodide

(2Z,7E)-(4R,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-6,8,10-trimethyl-undeca-2,7-dien-4-ol

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

Downstream raw materials:

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

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

(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

(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