(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

Base Information

Chemical Name:(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one
CAS No.:899436-60-3
Molecular Formula:C₂₇H₂₈O₆
Molecular Weight:448.516
Hs Code.:

Synonyms:(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

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Chemical Property of (4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

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Technology Process of (4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

There total 13 articles about (4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-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: 70.0%

: 899436-56-7
(S)-3-[(4S,5R,6R)-5-Benzyloxy-6-((R)-benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-propionic acid ethyl ester

: 899436-60-3
(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

Guidance literature:: With acetic acid; for 6h;
DOI:10.1016/j.tetlet.2006.04.146

Reference yield:

: 1053608-54-0
(4R,5S,6R)-5-Benzyloxy-6-((R)-benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxane-4-carbaldehyde

: 899436-60-3
(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: BF₃*OEt₂; 4 Angstroem MS / CH₂Cl₂ / 0 - 20 °C

2: LiEt₃BH / tetrahydrofuran / -78 °C

3: 70 percent / aq. AcOH / 6 h

With 4 Angstroem MS; boron trifluoride diethyl etherate; lithium triethylborohydride; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2006.04.146

Reference yield:

: 899436-58-9
(2S,3R,4R,5R)-3,5-Bis-benzyloxy-5-phenyl-pentane-1,2,4-triol

: 899436-60-3
(4S,5S)-5-((1S,2R,3R)-1,3-Bis-benzyloxy-2-hydroxy-3-phenyl-propyl)-4-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / imidazole / CH₂Cl₂

2: 85 percent / PPTS / CH₂Cl₂ / 20 °C

3: 90 percent / TBAF / tetrahydrofuran / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5: BF₃*OEt₂; 4 Angstroem MS / CH₂Cl₂ / 0 - 20 °C

6: LiEt₃BH / tetrahydrofuran / -78 °C

7: 70 percent / aq. AcOH / 6 h

With 1H-imidazole; oxalyl dichloride; 4 Angstroem MS; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium triethylborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 4: Swern oxidation;
DOI:10.1016/j.tetlet.2006.04.146