(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Base Information

Chemical Name:(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol
CAS No.:128856-00-8
Molecular Formula:C₃₉H₅₈O₈S
Molecular Weight:686.951
Hs Code.:

(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Synonyms:(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-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-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-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-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

There total 30 articles about (2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-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: 84.0%

: 128855-99-2
(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-2-Benzenesulfinyl-3-hydroxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

: 128856-00-8
(2R,3R)-2-[(4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: With trifluoroacetic anhydride; sodium iodide; In acetone; at 0 ℃; for 0.0833333h;
DOI:10.1007/BF00963026

Reference yield:

: 128855-99-2
(2R,3R)-2-[(2R,4R,5S,6R)-6-{(1S,2R,3S)-2-Benzenesulfinyl-3-hydroxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

: 128856-00-8
(2R,3R)-2-[(2R,4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: With trifluoroacetic anhydride; sodium iodide; In acetone; at 0 ℃; for 0.0833333h; Yield given;
DOI:10.1016/S0040-4020(01)81090-5

Reference yield:

: (2S,3S,4S,5R)-5-[1,3]Dithiolan-2-yl-3-methyl-hexane-1,2,4-triol

: 128856-00-8
(2R,3R)-2-[(2R,4R,5S,6R)-6-{(1S,2R,3S)-3-Hydroxy-1-methyl-2-phenylsulfanyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentane-2,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 2 h / -10 °C

2: TsOH*H₂O / acetone / 0.5 h / Ambient temperature

3: 77 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 84 h / Ambient temperature

4: benzene / Heating

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

6: tetrahydrofuran / 1.) -70 deg C, 2.) room temp., 30 min

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

8: 95 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

9: 1.) i-Pr₂NH, 0.85 N n-BuLi/hexane / 1.) THF, -60 deg C, 1 h, 2.) THF, -78 deg C, 2 h

10: NaI, TFAA / acetone / 0.08 h / 0 °C

With pyridine; n-butyllithium; oxalyl dichloride; hexane; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; trifluoroacetic anhydride; calcium carbonate; sodium iodide; mercury dichloride; In tetrahydrofuran; methanol; water; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)81090-5