(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol
CAS No.:532932-85-7
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

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Chemical Property of (2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

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Technology Process of (2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

There total 7 articles about (2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol 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: 34.0%

: 67-56-1
methanol

: 532932-80-2
(4S)-4-[(1'S,3'Z,5'RS)-5'-hydroxy-5'-phenyl-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane

: (2R,6S)-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-6-phenyl-3,6-dihydro-2H-pyran

: 532932-85-7
(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

: 532932-84-6
(2S,3S,4R,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3-methoxy-2-phenyltetrahydro-2H-pyran-4-ol

Guidance literature:: (4S)-4-[(1'S,3'Z,5'RS)-5'-hydroxy-5'-phenyl-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane; With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; cummene hydroperoxide; In dichloromethane; at -10 ℃; for 48h;

methanol; With potassium carbonate; for 4h; Heating;
DOI:10.1016/S0957-4166(03)00038-7

Reference yield:

: 93367-10-3,212375-57-0
(2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol

: 532932-85-7
(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 51 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 6 h / -78 °C

2.1: 80 percent / Et₃N / CH₂Cl₂ / 6 h / 20 °C

3.1: 71 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

4.1: 94 percent / quinoline; H₂ / Lindlar's catalyst / ethyl acetate / 6 h / 20 °C

5.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

6.1: 0.42 g / tetrahydrofuran / 3 h / 20 °C

7.1: Ti(O-iPr)4; (+)-DIPT; cummene hydroperoxide / CH₂Cl₂ / 48 h / -10 °C

7.2: 12 percent / K₂CO₃ / 4 h / Heating

With quinoline; titanium(IV) isopropylate; n-butyllithium; L-(+)-diisopropyl tartrate; cummene hydroperoxide; boron trifluoride diethyl etherate; hydrogen; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; 6.1: Grignard reaction / 7.1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0957-4166(03)00038-7

Reference yield:

: 532932-77-7
(4S)-4-[(1'S)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane

: 532932-85-7
(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / quinoline; H₂ / Lindlar's catalyst / ethyl acetate / 6 h / 20 °C

2.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3.1: 0.42 g / tetrahydrofuran / 3 h / 20 °C

4.1: Ti(O-iPr)4; (+)-DIPT; cummene hydroperoxide / CH₂Cl₂ / 48 h / -10 °C

4.2: 12 percent / K₂CO₃ / 4 h / Heating

With quinoline; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; cummene hydroperoxide; hydrogen; pyridinium chlorochromate; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate; 3.1: Grignard reaction / 4.1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0957-4166(03)00038-7