(E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid

Base Information

• Chemical Name: (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid
• CAS No.: 866416-01-5
• Molecular Formula: C₄₈H₈₄O₈SSi
• Molecular Weight: 849.342
• Mol file: 866416-01-5.mol

Synonyms:(E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid

Chemical Property of (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid

There total 33 articles about (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid 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: 80.0%

(E)-(5R,16R)-5-(tert-Butyl-dimethyl-silanyloxy)-16-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-3-phenylsulfanyl-oxacyclohexadec-13-en-2-one (866416-00-4) → (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid (866416-01-5)

Guidance literature:

With lithium hydroxide; (1,4,7,10-tetraoxacyclododecane); In tetrahydrofuran; methanol; Heating;

DOI:10.1016/j.tetlet.2005.07.148

Reference yield:

(E)-3-hexene-1,6-dioic acid (29311-53-3) → (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid (866416-01-5)

Guidance literature:

Multi-step reaction with 28 steps

1.1: H₂SO₄ / benzene / 48 h / Heating

2.1: LAH / diethyl ether / 0 - 20 °C

3.1: pyridine / CH₂Cl₂ / 10 h / 0 - 20 °C

4.1: 99 percent / K₃FeCN₆; NaHCO₃; K₂CO₃ / OsO₄; DHQ₂(PHAL) / H₂O; 2-methyl-propan-2-ol / 12 h / 0 °C

5.1: CSA / CH₂Cl₂ / 20 °C

6.1: TiCl₄; NaBH₃CN; TEA / acetonitrile / 0.83 h / 0 °C

7.1: LAH / diethyl ether / 0 - 20 °C

8.1: CSA / CH₂Cl₂ / 20 °C

9.1: I₂; Ph₃P; imidazole / CH₂Cl₂ / 20 °C

10.1: n-BuLi / tetrahydrofuran

10.2: HMPA / tetrahydrofuran / -30 - 20 °C

11.1: DDQ / CH₂Cl₂; H₂O / 20 °C

12.1: NMM / acetonitrile; CH₂Cl₂ / 20 °C

13.1: MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

14.1: 93 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / 0 °C

15.1: DIPEA / CH₂Cl₂ / 0 - 20 °C

16.1: LAH / diethyl ether / 0 - 20 °C

17.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

18.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

19.1: DIBAL / CH₂Cl₂ / 0 °C

19.2: H₂ / Pd-C / methanol / 20 °C

20.1: n-Bu₂SnO; TEA / 10 h / 20 °C

21.1: NMM / CH₂Cl₂ / 24 h / 0 - 20 °C

22.1: NaI / acetone / 16 h / Heating

23.1: 93 percent / n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -30 °C

24.1: TFAA; 2,4,6-collidine / 0.17 h / 0 °C

24.2: 82 percent / K₂CO₃ / aq. phosphate buffer / 0.5 h / 0 °C / pH 7.0

25.1: 4 Angstroem MS / toluene / 3 h / -78 °C

26.1: DMAP / benzene

27.1: 94 percent / (PCy₃P)2(Cl)2Ru=CHPh / CH₂Cl₂ / 16 h / 20 °C

28.1: 80 percent / LiOH; 12-crown-4 / methanol; tetrahydrofuran / Heating

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; lithium hydroxide; lithium aluminium tetrahydride; Grubbs catalyst first generation; n-butyllithium; samarium diiodide; (1,4,7,10-tetraoxacyclododecane); triethyl borane; 4 Angstroem MS; TEA; sulfuric acid; camphor-10-sulfonic acid; iodine; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; potassium hexacyanoferrate(III); methyl iodide; osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 18.1: Wittig reaction / 24.1: Pummerer rearrangement / 24.2: Pummerer rearrangement / 26.1: Yamaguchi esterification;

DOI:10.1016/j.tetlet.2005.07.148

Reference yield:

Diethyl trans-hex-3-enedioate (57042-08-7) → (E)-(4R,15R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-15-hydroxy-2-phenylsulfanyl-pentadec-12-enoic acid (866416-01-5)

Guidance literature:

Multi-step reaction with 27 steps

1.1: LAH / diethyl ether / 0 - 20 °C

2.1: pyridine / CH₂Cl₂ / 10 h / 0 - 20 °C

3.1: 99 percent / K₃FeCN₆; NaHCO₃; K₂CO₃ / OsO₄; DHQ₂(PHAL) / H₂O; 2-methyl-propan-2-ol / 12 h / 0 °C

4.1: CSA / CH₂Cl₂ / 20 °C

5.1: TiCl₄; NaBH₃CN; TEA / acetonitrile / 0.83 h / 0 °C

6.1: LAH / diethyl ether / 0 - 20 °C

7.1: CSA / CH₂Cl₂ / 20 °C

8.1: I₂; Ph₃P; imidazole / CH₂Cl₂ / 20 °C

9.1: n-BuLi / tetrahydrofuran

9.2: HMPA / tetrahydrofuran / -30 - 20 °C

10.1: DDQ / CH₂Cl₂; H₂O / 20 °C

11.1: NMM / acetonitrile; CH₂Cl₂ / 20 °C

12.1: MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

13.1: 93 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / 0 °C

14.1: DIPEA / CH₂Cl₂ / 0 - 20 °C

15.1: LAH / diethyl ether / 0 - 20 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

17.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

18.1: DIBAL / CH₂Cl₂ / 0 °C

18.2: H₂ / Pd-C / methanol / 20 °C

19.1: n-Bu₂SnO; TEA / 10 h / 20 °C

20.1: NMM / CH₂Cl₂ / 24 h / 0 - 20 °C

21.1: NaI / acetone / 16 h / Heating

22.1: 93 percent / n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -30 °C

23.1: TFAA; 2,4,6-collidine / 0.17 h / 0 °C

23.2: 82 percent / K₂CO₃ / aq. phosphate buffer / 0.5 h / 0 °C / pH 7.0

24.1: 4 Angstroem MS / toluene / 3 h / -78 °C

25.1: DMAP / benzene

26.1: 94 percent / (PCy₃P)2(Cl)2Ru=CHPh / CH₂Cl₂ / 16 h / 20 °C

27.1: 80 percent / LiOH; 12-crown-4 / methanol; tetrahydrofuran / Heating

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; lithium hydroxide; lithium aluminium tetrahydride; Grubbs catalyst first generation; n-butyllithium; samarium diiodide; (1,4,7,10-tetraoxacyclododecane); triethyl borane; 4 Angstroem MS; TEA; camphor-10-sulfonic acid; iodine; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; potassium hexacyanoferrate(III); methyl iodide; osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 3.1: Sharpless asymmetric dihydroxylation / 17.1: Wittig reaction / 23.1: Pummerer rearrangement / 23.2: Pummerer rearrangement / 25.1: Yamaguchi esterification;

DOI:10.1016/j.tetlet.2005.07.148

upstream raw materials:

(E)-(5R,16R)-5-(tert-Butyl-dimethyl-silanyloxy)-16-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-3-phenylsulfanyl-oxacyclohexadec-13-en-2-one

(R)-2-(non-8-enyl)oxirane

(3S,4S)-4-(4-Methoxy-benzyloxy)-hexane-1,3,6-triol

(E)-3-[(S)-4-Oxo-1-((2S,4S)-2-phenyl-[1,3]dioxan-4-yl)-butoxy]-acrylic acid ethyl ester