(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

Base Information

Chemical Name:(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone
CAS No.:906098-18-8
Molecular Formula:C₁₄H₁₆O₄
Molecular Weight:248.279
Hs Code.:

Synonyms:(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

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Chemical Property of (4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

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Technology Process of (4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

There total 8 articles about (4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone 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: 70.0%

: 906098-15-5
methyl (3S,4R,5R,6S)-3-phenyl-4,5,6-tris(methoxymethoxy)-7-octenoate

: 906098-18-8
(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

Guidance literature:: With hydrogenchloride; In methanol; at 60 ℃; for 3h;
DOI:10.1021/jo0607562

Reference yield:

: 906098-12-2
benzyl 2,3,4-tri-O-methoxymethyl-D-xylopyranoside

: 906098-18-8
(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 61.3 percent / H₂ / Pd/C / tetrahydrofuran / 12 h / 2068.59 Torr

2.1: BuLi / tetrahydrofuran; hexane / 2 h / 20 °C

2.2: 60.8 percent / tetrahydrofuran; hexane / 45 - 50 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.1: 1.48 g / CH₂Cl₂ / 10 h / -78 - 20 °C

5.1: Mg / tetrahydrofuran / Heating

5.2: CuI / tetrahydrofuran / 0.5 h / -20 °C

5.3: 46 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

6.1: 70 percent / aq. HCl / methanol / 3 h / 60 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.2: Wittig methylenation / 3.1: Swern oxidation / 4.1: Wittig olefination;
DOI:10.1021/jo0607562

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 906098-18-8
(4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 73.8 percent / AcCl / 24 h / 50 °C

2.1: 82 percent / iPr₂NEt / CH₂Cl₂ / 12 h / 20 °C

3.1: 61.3 percent / H₂ / Pd/C / tetrahydrofuran / 12 h / 2068.59 Torr

4.1: BuLi / tetrahydrofuran; hexane / 2 h / 20 °C

4.2: 60.8 percent / tetrahydrofuran; hexane / 45 - 50 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

6.1: 1.48 g / CH₂Cl₂ / 10 h / -78 - 20 °C

7.1: Mg / tetrahydrofuran / Heating

7.2: CuI / tetrahydrofuran / 0.5 h / -20 °C

7.3: 46 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

8.1: 70 percent / aq. HCl / methanol / 3 h / 60 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; magnesium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.2: Wittig methylenation / 5.1: Swern oxidation / 6.1: Wittig olefination;
DOI:10.1021/jo0607562