(Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

Base Information

• Chemical Name: (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one
• CAS No.: 312695-97-9
• Molecular Formula: C₃₈H₅₀O₈
• Molecular Weight: 634.81
• Mol file: 312695-97-9.mol

Synonyms:(Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

Chemical Property of (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

There total 60 articles about (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one 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: 88.0%

(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one (312695-96-8) → (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.08,10]docosa-15,19-dien-14-one (312695-97-9)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dodecane; dichloromethane; at -20 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja907924j

Reference yield:

(2S)-2-(2,2-dibromo-vinyl)-4-methyl-3,6-dihydro-2H-pyran (289472-92-0) → (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.08,10]docosa-15,19-dien-14-one (312695-97-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

1.2: 64 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

3.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

4.1: 81 percent / Red-Al / tetrahydrofuran / -40 - -20 °C

5.1: TFA / CH₂Cl₂ / 1 h / 23 °C

6.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

7.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

8.1: PPTS / CH₂Cl₂ / 5 h / 23 °C

9.1: 102 mg / TBAF / tetrahydrofuran / 3 h / 23 °C

10.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

11.1: 89 percent / Ph₃P; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h

12.2: 75 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.1: CSA / methanol

14.1: 22 mg / LiOH / tetrahydrofuran; H₂O / 2 h

15.1: trichlorobenzoyl chloride; iPr₂NEt / tetrahydrofuran; benzene / 0.5 h

15.2: 68 percent / DMAP / benzene / 12 h

16.1: 94 percent / H₂; 1-hexene / Lindlar catalyst / ethyl acetate / 1.5 h

17.1: 45 percent / PPTS / 2-methyl-propan-2-ol / 8 h / 83 °C

18.1: Ti(OiPr)4; diethyl D-(+)-tartrate; tert-butyl hydroperoxide / CH₂Cl₂; decane / 1 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; n-butyllithium; 1-hexene; trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1021/jo010854h

Reference yield:

(E)-(3S,4S)-6-Benzenesulfonyl-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-ene-3,4-diol → (Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.08,10]docosa-15,19-dien-14-one (312695-97-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

2.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

3.1: PPTS / CH₂Cl₂ / 5 h / 23 °C

4.1: 102 mg / TBAF / tetrahydrofuran / 3 h / 23 °C

5.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

6.1: 89 percent / Ph₃P; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h

7.2: 75 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: CSA / methanol

9.1: 22 mg / LiOH / tetrahydrofuran; H₂O / 2 h

10.1: trichlorobenzoyl chloride; iPr₂NEt / tetrahydrofuran; benzene / 0.5 h

10.2: 68 percent / DMAP / benzene / 12 h

11.1: 94 percent / H₂; 1-hexene / Lindlar catalyst / ethyl acetate / 1.5 h

12.1: 45 percent / PPTS / 2-methyl-propan-2-ol / 8 h / 83 °C

13.1: Ti(OiPr)4; diethyl D-(+)-tartrate; tert-butyl hydroperoxide / CH₂Cl₂; decane / 1 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; n-butyllithium; 1-hexene; trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1021/jo010854h

upstream raw materials:

(1R,3Z,7S,9E,11S,15S,17R)-11-hydroxy-7-{(1S,2E)-1-(4-methoxybenzyloxy)-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]allyl}-15-methyl-13-methylene-6,21-dioxabicyclo[15.3.1]henicosa-3,9,19-trien-5-one

[(2R,4S)-4-(1-Ethoxy-allyloxy)-2-methyl-hept-6-enyloxymethyl]-benzene

[3R]-4-Benzyloxy-3-methylbutanal

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

Downstream raw materials:

laulimalide

Refernces

• 1、 Trost, Barry M.,Amans, Dominique,Seganish, W. Michael,Chung, Cheol K.. "Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide". supporting information; experimental part. p. 17087 - 17089. Retrieved 2010/03/23.
• 2、 Ghosh,Wang. "Total synthesis of (-)-laulimalide [12]". . p. 11027 - 11028. Retrieved 2007/10/03.