(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester
CAS No.:237056-53-0
Molecular Formula:C₃₀H₅₀O₆S
Molecular Weight:538.789
Hs Code.:

(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

Synonyms:(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

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Chemical Property of (2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

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Technology Process of (2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

There total 14 articles about (2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl 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: 92.0%

: 97250-84-5
tert-Butyl-((E)-1-tert-butylsulfanyl-propenyloxy)-dimethyl-silane

: 237056-52-9
(2R,3S,4S)-2,4-dimethyl-3-(p-methoxybenzyloxy)-6-((2S,4R,6S)-4-methoxy-6-methyltetrahydropyran-2-yl)hexanal

: 237056-53-0
(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.75h;
DOI:10.1021/jo990291y

Reference yield:

: 136521-65-8
(4S,6S)-4-Hydroxy-6-(benzyloxy)-1-heptene

: 237056-53-0
(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) KH / 1.) THF, 0 deg C, 20 min, 2.) room temperature, 1 h

2: 96 percent / Li/NH₃ / 4 h / -78 - 20 °C

3: 1.) O₃, 2.) DMS / 1.) -78 deg C, 2.) room temperature, 12 h

4: 84 percent / TMSOTf / acetonitrile / 0.25 h

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) room temperature, 2.5 h

6: 1.) TiCl₄, i-Pr₂NEt / 1.) CH₂Cl₂, -5 deg C, 1 h, 2.) -78 deg C, 2.5 h; -40 deg C, 1.5 h

7: 90 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 45 h

8: LiBH₄ / tetrahydrofuran / 1 h / 0 °C

9: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.67 h

10: 86 percent / tetrahydrofuran / 40 h / Heating

11: 100 percent / Bu₃SnH / toluene / 0.5 h / Heating

12: 91 percent / DIBAL / CH₂Cl₂; toluene / 1.5 h / 0 °C

13: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h

14: 92 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.75 h / -78 °C

With lithium borohydride; 2,3-dimercapto-succinic acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; tri-n-butyl-tin hydride; titanium tetrachloride; lithium; potassium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; toluene; acetonitrile;
DOI:10.1021/jo990291y

Reference yield:

: 142144-27-2
(2R,4R,6S)-4-(dimethoxy)-6-methyl-2-(prop-1-enyl)tetrahydropyran

: 237056-53-0
(2R,3R,4R,5S,6S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-8-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-octanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) room temperature, 2.5 h

2: 1.) TiCl₄, i-Pr₂NEt / 1.) CH₂Cl₂, -5 deg C, 1 h, 2.) -78 deg C, 2.5 h; -40 deg C, 1.5 h

3: 90 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 45 h

4: LiBH₄ / tetrahydrofuran / 1 h / 0 °C

5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.67 h

6: 86 percent / tetrahydrofuran / 40 h / Heating

7: 100 percent / Bu₃SnH / toluene / 0.5 h / Heating

8: 91 percent / DIBAL / CH₂Cl₂; toluene / 1.5 h / 0 °C

9: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h

10: 92 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.75 h / -78 °C

With lithium borohydride; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; toluene; acetonitrile;
DOI:10.1021/jo990291y