(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

Base Information

Chemical Name:(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide
CAS No.:153000-34-1
Molecular Formula:C₂₀H₂₀O₅
Molecular Weight:340.376
Hs Code.:

Synonyms:(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

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Chemical Property of (+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

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Technology Process of (+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

There total 8 articles about (+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide 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: 94.0%

: 153000-32-9
(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

: 153000-34-1
(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

Guidance literature:: With boron trifluoride diethyl etherate; sodium iodide; In acetonitrile;
DOI:10.1016/S0040-4039(00)61733-1

Reference yield:

: 145041-33-4
S-tert-butyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanethioate

: 153000-34-1
(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

Guidance literature:: Multi-step reaction with 4 steps

1: DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

2: DIBAL-H / toluene / 0.5 h / 0 °C

3: Ti(Oi-Pr)2Cl₂ / CH₂Cl₂ / 1 h / -78 °C

4: 94 percent / NaI, BF₃*OEt₂ / acetonitrile / 0.5 h / 0 °C

With dmap; titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium iodide; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/0040-4020(96)00296-7

Reference yield:

: 153063-58-2
methyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanoate

: 153000-34-1
(+)-(1'S,2'R,3'R,4R)-4-(2'-benzyloxy-1',3'-dihydroxy-3'-phenylpropyl)-2-buten-4-olide

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

2: DIBAL-H / toluene / 0.5 h / 0 °C

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

4: Ti(Oi-Pr)2Cl₂ / CH₂Cl₂ / 1 h / -78 °C

5: 94 percent / NaI, BF₃*OEt₂ / acetonitrile / 0.5 h / 0 °C

With dmap; titanium(IV) dichlorodiisopropylate; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; dimethyl sulfoxide; sodium iodide; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/0040-4020(96)00296-7