(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

Base Information

Chemical Name:(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester
CAS No.:130543-45-2
Molecular Formula:C₄₄H₄₆O₇
Molecular Weight:686.845
Hs Code.:

Synonyms:(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

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Chemical Property of (4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

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Technology Process of (4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

There total 8 articles about (4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester 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: 50.0%

: 130543-50-9
2-bromomethylacrylic acid benzyl ester

: 116087-65-1
(2S,3R,4R)-2,3,4,5-tetrakis(benzyloxy)pentanal

: 130543-45-2
(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

: 130559-18-1
(4S,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

Guidance literature:: With chromium dichloride; In tetrahydrofuran; for 1.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)85595-2

Reference yield:

: 100-39-0
benzyl bromide

: 130543-45-2
(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2) rt, 6 h

3: 44 percent / CrCl₂ / tetrahydrofuran / 1.5 h / Ambient temperature

With chromium dichloride; dimethylsulfide; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)85595-2

Reference yield:

: 130543-49-6
(2E,5E)-1,7-Bis-benzyloxy-hepta-2,5-dien-4-ol

: 130543-45-2
(4R,5R,6R,7R)-5,6,7,8-Tetrakis-benzyloxy-4-hydroxy-2-methylene-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / 1.) D-(-)-diisoprop
2: 90 percent / pyridine / CH₂Cl₂ / Ambient temperature

3: 1.) BF₃*OEt₂, 2.) H₂SO₄ / 1.) ether, -20 deg C, 2 h, 2.) rt, 5 h

4: 97 percent / NaOMe / methanol / 5 h / Ambient temperature

5: 95 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Ambient temperature

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2) rt, 6 h

7: 44 percent / CrCl₂ / tetrahydrofuran / 1.5 h / Ambient temperature

With pyridine; chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; D-(-)-diisopropyl tartrate; ozone; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)85595-2