(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester

Base Information

• Chemical Name: (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester
• CAS No.: 866415-98-7
• Molecular Formula: C₅₀H₈₆O₇SSi
• Molecular Weight: 859.38

Synonyms:(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester

Chemical Property of (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester

There total 30 articles about (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester 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:

(E)-3-hexene-1,6-dioic acid (29311-53-3) → (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester (866415-98-7)

Guidance literature:

Multi-step reaction with 26 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; 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; 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) → (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester (866415-98-7)

Guidance literature:

Multi-step reaction with 25 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; 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; 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

Reference yield:

(E)-hex-3-ene-1,6-diyl dibenzoate (193354-06-2) → (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-tridec-12-enoic acid (R)-1-[(2R,5S)-5-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-enyl ester (866415-98-7)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 99 percent / K₃FeCN₆; NaHCO₃; K₂CO₃ / OsO₄; DHQ₂(PHAL) / H₂O; 2-methyl-propan-2-ol / 12 h / 0 °C

2.1: CSA / CH₂Cl₂ / 20 °C

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

4.1: LAH / diethyl ether / 0 - 20 °C

5.1: CSA / CH₂Cl₂ / 20 °C

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

7.1: n-BuLi / tetrahydrofuran

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

8.1: DDQ / CH₂Cl₂; H₂O / 20 °C

9.1: NMM / acetonitrile; CH₂Cl₂ / 20 °C

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

11.1: 93 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / 0 °C

12.1: DIPEA / CH₂Cl₂ / 0 - 20 °C

13.1: LAH / diethyl ether / 0 - 20 °C

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

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

16.1: DIBAL / CH₂Cl₂ / 0 °C

16.2: H₂ / Pd-C / methanol / 20 °C

17.1: n-Bu₂SnO; TEA / 10 h / 20 °C

18.1: NMM / CH₂Cl₂ / 24 h / 0 - 20 °C

19.1: NaI / acetone / 16 h / Heating

20.1: 93 percent / n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -30 °C

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

21.2: 82 percent / K₂CO₃ / aq. phosphate buffer / 0.5 h / 0 °C / pH 7.0

22.1: 4 Angstroem MS / toluene / 3 h / -78 °C

23.1: DMAP / benzene

With 4-methyl-morpholine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; 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; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: Sharpless asymmetric dihydroxylation / 15.1: Wittig reaction / 21.1: Pummerer rearrangement / 21.2: Pummerer rearrangement / 23.1: Yamaguchi esterification;

DOI:10.1016/j.tetlet.2005.07.148

upstream raw materials:

(R)-1-[(2R,5S)-5-((2S,5R,6S)-6-Decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-tetrahydro-furan-2-yl]-but-3-en-1-ol

(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

Downstream 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

(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

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