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

Base Information

• Chemical Name: (E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol
• CAS No.: 130740-38-4
• Molecular Formula: C₂₅H₄₂O₆
• Molecular Weight: 438.605
• Mol file: 130740-38-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 36 articles about (E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol 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:

2,2-Dimethyl-propionic acid (2R,3S)-4-benzyloxy-2-methoxymethoxy-3-methyl-butyl ester → (E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-38-4,130852-78-7)

Guidance literature:

Multi-step reaction with 17 steps

1: LiAlH₄

2: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

4: MnO₂

6: LiAlH₄

7: KH

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

9: KH

10: LiAlH₄ / H₂O; trifluoroacetic acid

11: Swern oxidation

12: ZnCl₂ / diethyl ether

13: H₂ / Lindlar

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

15: 75 percent / Mo(CO)6, TBHP / benzene

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

17: LiBH₄ / tetrahydrofuran / 65 °C

With tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; lithium borohydride; oxalyl dichloride; hexacarbonyl molybdenum; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; 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

Reference yield:

(E)-(2R,3S,6R,7S)-8-Benzyloxy-2-methoxy-6-methoxymethoxy-3,5,7-trimethyl-oct-4-en-1-ol (130740-47-5) → (E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-38-4,130852-78-7)

Guidance literature:

Multi-step reaction with 7 steps

1: Swern oxidation

2: ZnCl₂ / diethyl ether

3: H₂ / Lindlar

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

5: 75 percent / Mo(CO)6, TBHP / benzene

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

7: LiBH₄ / tetrahydrofuran / 65 °C

With tert.-butylhydroperoxide; lithium borohydride; hexacarbonyl molybdenum; hydrogen; potassium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; benzene;

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

Reference yield:

(E)-(2R,3S,6R,7S)-8-Benzyloxy-2-methoxy-6-methoxymethoxy-3,5,7-trimethyl-oct-4-enal → (E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-38-4,130852-78-7)

Guidance literature:

Multi-step reaction with 6 steps

1: ZnCl₂ / diethyl ether

2: H₂ / Lindlar

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

4: 75 percent / Mo(CO)6, TBHP / benzene

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

6: LiBH₄ / tetrahydrofuran / 65 °C

With tert.-butylhydroperoxide; lithium borohydride; hexacarbonyl molybdenum; hydrogen; potassium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; benzene;

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

upstream raw materials:

(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

(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:

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

(3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one

(E)-(1R,2R,4R,5S,6R,9S,10R)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol

(E)-(1R,2S,4S,5R,6S,9R,10S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol