(5S,6R,7R,8R)-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,8R)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one
• CAS No.: 153619-50-2
• Molecular Formula: C₁₇H₂₂O₇
• Molecular Weight: 338.357
• Mol file: 153619-50-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R,7R,8R)-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,8R)-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%

(S)-Methoxymethoxy-((2R,3S)-3-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-acetaldehyde (153619-46-6) → (5S,6R,7R,8R)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one (153619-50-2) + (5S,6R,7R,8S)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one (153619-51-3)

Guidance literature:

With triethylamine; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00023-X

Reference yield:

(1S,2R)-1-(2-furyl)-2,3-(dimethylmethylen-dioxy)-1-propanol (80541-30-6) → (5S,6R,7R,8R)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one (153619-50-2)

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: 78 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:

(5S,6R)-6-<(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-5-hydroxy-5,6-dihydro-2H-pyran-2-one (147958-05-2) → (5S,6R,7R,8R)-6-<7,8-dihydro-8-hydroxy-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one (153619-50-2)

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: 78 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

upstream raw materials:

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

(1S,2R)-1-(2-furyl)-2,3-(dimethylmethylen-dioxy)-1-propanol

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

(5S,6R)-6-<(1'R)-1',2'-dihydroxyethyl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

Downstream raw materials:

(+)-goniofufurone

8-epi-goniopypyrone-5,7-O-dimethoxymethyl ether

(5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one

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