(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one
CAS No.:153619-51-3
Molecular Formula:C₁₇H₂₂O₇
Molecular Weight:338.357
Hs Code.:

Synonyms:(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

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Technology Process of (5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

There total 9 articles about (5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one 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: 78.0%

: 153619-46-6
(S)-Methoxymethoxy-((2R,3S)-3-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-acetaldehyde

: 153619-50-2
(5S,6R,7R,8R)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

: 153619-51-3
(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With triethylamine; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(99)00023-X

Reference yield:

: 80541-30-6
(1S,2R)-1-(2-furyl)-2,3-(dimethylmethylen-dioxy)-1-propanol

: 153619-51-3
(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / NBS, NaOAc / tetrahydrofuran; H₂O / 0.5 h / 0 °C

2: CrO₃ / acetic acid / 0.5 h / Ambient temperature

3: sodium triacetoxyborohydride / propan-2-ol / 0.5 h / -20 °C

4: 83 percent / iPr₂EtN, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

5: 88 percent / AcOH, H₂O / tetrahydrofuran / 8 h / 40 °C

6: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

7: 99 percent / iPr₂EtN, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

8: 98 percent / AcOH, H₂O / tetrahydrofuran / 5 h / 40 °C

9: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h

10: 19 percent / Et₃N / 2 h / 0 °C

With chromium(VI) oxide; dmap; N-Bromosuccinimide; oxalyl dichloride; water; sodium acetate; sodium tris(acetoxy)borohydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; isopropyl alcohol;
DOI:10.1016/S0040-4020(99)00023-X

Reference yield:

: 147958-05-2
(5S,6R)-6-<(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-5-hydroxy-5,6-dihydro-2H-pyran-2-one

: 153619-51-3
(5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / iPr₂EtN, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

2: 88 percent / AcOH, H₂O / tetrahydrofuran / 8 h / 40 °C

3: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

4: 99 percent / iPr₂EtN, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

5: 98 percent / AcOH, H₂O / tetrahydrofuran / 5 h / 40 °C

6: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h

7: 19 percent / Et₃N / 2 h / 0 °C

With dmap; oxalyl dichloride; water; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(99)00023-X