(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

Base Information

Chemical Name:(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate
CAS No.:141192-98-5
Molecular Formula:C₂₉H₃₈O₇SSi
Molecular Weight:558.768
Hs Code.:

(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

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Chemical Property of (2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

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Technology Process of (2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

There total 13 articles about (2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate 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: 10.0%

: 141192-97-4,147780-55-0
(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 141192-98-5,147780-56-1
(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

: 141208-39-1,147780-57-2
C₃₆H₄₄O₉S₂Si

Guidance literature:: With dmap; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4020(01)80546-9

Reference yield:

: 55174-91-9
(-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose

: 141192-98-5,147780-56-1
(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) -20 deg C, 1 h

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min

3: Bu₄NF / tetrahydrofuran / 1 h / 0 °C

4: 77 percent / K₂CO₃ / acetone / 144 h / 70 °C

5: 88 percent / TFA / H₂O / 2 h / Ambient temperature

6: 62 percent / 2,6-lutidine / CH₂Cl₂ / 1) -78 deg C, 2 h, 2) -78 to 0 deg C

8: 81 percent / CuI, Et₂NH / Pd(PPh₃)4 / dimethylformamide / 0.5 h / Ambient temperature

9: 55 percent / DMAP / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; dmap; copper(l) iodide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)80546-9

Reference yield:

: 55174-92-0
1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose

: 141192-98-5,147780-56-1
(2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-hydroxy-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1-yl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min

2: Bu₄NF / tetrahydrofuran / 1 h / 0 °C

3: 77 percent / K₂CO₃ / acetone / 144 h / 70 °C

4: 88 percent / TFA / H₂O / 2 h / Ambient temperature

5: 62 percent / 2,6-lutidine / CH₂Cl₂ / 1) -78 deg C, 2 h, 2) -78 to 0 deg C

7: 81 percent / CuI, Et₂NH / Pd(PPh₃)4 / dimethylformamide / 0.5 h / Ambient temperature

8: 55 percent / DMAP / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; dmap; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; potassium carbonate; diethylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)80546-9