(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

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Chemical Name:(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester
CAS No.:856426-94-3
Molecular Formula:C₃₈H₅₂O₈S
Molecular Weight:668.892
Hs Code.:

(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

Synonyms:(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

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Chemical Property of (E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

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Technology Process of (E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

There total 22 articles about (E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl 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: 47.0%

: 856426-93-2
(2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 922-67-8
propynoic acid methyl ester

: 856426-94-3
(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: With trimethylphosphane; In dichloromethane; at 20 ℃;
DOI:10.1021/ol050760k

Reference yield:

: 1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-ol

: 856426-94-3
(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: 2.89 g / tetra-n-propylammonium perruthenate; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

3.1: 87 percent / 4-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

4.1: 99 percent / SmI₂ / tetrahydrofuran; methanol / 0.25 h / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 13 h / 0 - 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

7.1: NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

7.2: 0.61 g / tetrahydrofuran; CH₂Cl₂ / 9 h / 20 °C

8.1: 9-BBN-H / tetrahydrofuran / 4 h / 20 °C

8.2: 1.74 g / H₂O₂; aq. NaOH / tetrahydrofuran / 12 h / 20 °C

9.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 20 °C

10.1: 1.75 g / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

11.1: Et₃N / tetrahydrofuran / 1.5 h / 20 °C

12.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

13.1: DIBALH / CH₂Cl₂; hexane / 0.33 h / -78 °C

14.1: 0.42 g / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

15.1: TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0 - 20 °C

16.1: 0.11 g / TBAF / acetonitrile / 7 h / 70 °C

17.1: 47 percent / Me₃P / CH₂Cl₂; tetrahydrofuran / 11 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; trimethylphosphane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; 7.2: Wittig reaction / 9.1: Parikh-Doering oxidation;
DOI:10.1016/j.tet.2007.02.039

Reference yield:

: 856426-85-2
(E)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

: 856426-94-3
(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / TMSCl; bis(N-isopropylsalicylaldimine) copper(II) complex / tetrahydrofuran; diethyl ether / 1.5 h / -45 °C

2.1: 95 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: KOt-Bu / tetrahydrofuran / 0.17 h / 20 °C

3.2: 90 percent / Bu₄NI / tetrahydrofuran / 1 h / 20 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 0.33 h / -78 °C

7.1: 0.42 g / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

8.1: TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0 - 20 °C

9.1: 0.11 g / TBAF / acetonitrile / 7 h / 70 °C

10.1: 47 percent / Me₃P / CH₂Cl₂; tetrahydrofuran / 11 h / 20 °C

With pyridine; dmap; chloro-trimethyl-silane; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2007.02.039