(2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran
• CAS No.: 866415-93-2
• Molecular Formula: C₂₉H₄₇IO₅S
• Molecular Weight: 634.66

Synonyms:

Chemical Property of (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran

There total 22 articles about (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran 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-hexen-1,6-diol (71655-17-9) → (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran (866415-93-2)

Guidance literature:

Multi-step reaction with 20 steps

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

2.1: 99 percent / K₃FeCN₆; NaHCO₃; K₂CO₃ / OsO₄; DHQ₂(PHAL) / H₂O; 2-methyl-propan-2-ol / 12 h / 0 °C

3.1: CSA / CH₂Cl₂ / 20 °C

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

5.1: LAH / diethyl ether / 0 - 20 °C

6.1: CSA / CH₂Cl₂ / 20 °C

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

8.1: n-BuLi / tetrahydrofuran

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

9.1: DDQ / CH₂Cl₂; H₂O / 20 °C

10.1: NMM / acetonitrile; CH₂Cl₂ / 20 °C

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

12.1: 93 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / 0 °C

13.1: DIPEA / CH₂Cl₂ / 0 - 20 °C

14.1: LAH / diethyl ether / 0 - 20 °C

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

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

17.1: DIBAL / CH₂Cl₂ / 0 °C

17.2: H₂ / Pd-C / methanol / 20 °C

18.1: n-Bu₂SnO; TEA / 10 h / 20 °C

19.1: NMM / CH₂Cl₂ / 24 h / 0 - 20 °C

20.1: NaI / acetone / 16 h / Heating

With 4-methyl-morpholine; pyridine; 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; TEA; camphor-10-sulfonic acid; iodine; titanium tetrachloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation / 16.1: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.148

Reference yield:

(E)-3-hexene-1,6-dioic acid (29311-53-3) → (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran (866415-93-2)

Guidance literature:

Multi-step reaction with 22 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; TEA; sulfuric acid; camphor-10-sulfonic acid; iodine; titanium tetrachloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 18.1: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.148

Reference yield:

Diethyl trans-hex-3-enedioate (57042-08-7) → (2S,3R,6S)-2-Decyl-6-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-3-methoxymethoxy-tetrahydro-pyran (866415-93-2)

Guidance literature:

Multi-step reaction with 21 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; TEA; camphor-10-sulfonic acid; iodine; titanium tetrachloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 3.1: Sharpless asymmetric dihydroxylation / 17.1: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.148

upstream raw materials:

(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

[(2S,3R,6S)-3-Hydroxy-6-((2S,4S)-2-phenyl-[1,3]dioxan-4-yl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

(2S,4S)-4-[(S)-3-[1,3]Dithian-2-yl-1-(4-methoxy-benzyloxy)-propyl]-2-phenyl-[1,3]dioxane

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

(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

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