(2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Base Information

Chemical Name:(2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol
CAS No.:128879-56-1
Molecular Formula:C₂₆H₃₆O₆S
Molecular Weight:476.634
Hs Code.:

Synonyms:(2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

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Chemical Property of (2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

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Technology Process of (2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

There total 14 articles about (2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol 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: 100.0%

: 128879-55-0
(2R,4R,5S,6R)-4-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-6-[(1S,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

: 128879-56-1
(2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 100 ℃; for 30h;
DOI:10.1016/S0040-4020(01)81090-5

Reference yield: 100.0%

: 128879-55-0,129245-18-7,129245-19-8
(4R,5S,6R)-4-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-6-[(1S,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

: 128879-56-1,129269-52-9
(2R,3R)-2-[(4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 100 ℃; for 30h;
DOI:10.1007/BF00963026

Reference yield:

: 129245-11-0
Benzoic acid (2S,3R,4R,5R)-4,5-dihydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-heptyl ester

: 128879-56-1
(2R,3R)-2-[(2R,4R,5S,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / CH₂Cl₂ / 17 h / 100 °C

2: 15 percent NaOH / methanol / 1 h / Heating

3: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 40 min, 2.) CH₂Cl₂

4: 1.) 0.7 N n-BuLi/hexane / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

5: 82 percent / molecular sieves (3 Angstroem), DDQ / CH₂Cl₂ / 0.05 h / Ambient temperature

6: 82 percent / 1 N LiBHEt₃/THF / tetrahydrofuran / 120 h / Ambient temperature

7: 96 percent / n-Bu₃P / pyridine / 22 h / Ambient temperature

8: 65 percent / 85 percent MCPBA / ethyl acetate / 0.17 h / -40 °C

9: 75 percent / TFAA, 2,4,6-collidine / tetrahydrofuran / 0.33 h / -60 °C

10: 100 percent / (n-Bu)4NF*3H₂O / tetrahydrofuran / 30 h / 100 °C

With tetrahydrofuran; 2,4,6-trimethyl-pyridine; sodium hydroxide; n-butyllithium; oxalyl dichloride; hexane; tributylphosphine; 3 A molecular sieve; tetrabutyl ammonium fluoride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(01)81090-5