2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester
CAS No.:96212-59-8
Molecular Formula:C₂₃H₃₂O₆
Molecular Weight:404.503
Hs Code.:

2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

There total 20 articles about 2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl 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: 70.0%

: 96212-58-7
2,2-Dimethyl-propionic acid (1S,4R,5R,6S)-6-benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-5-hydroxy-4-methoxy-3-methyl-cyclohex-2-enylmethyl ester

: 96212-59-8
2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: With pyridine; p-toluenesulfonyl chloride;
DOI:10.1021/jo00209a050

Reference yield:

: 39838-77-2,51996-47-5
(3aR,5R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 96212-59-8
2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 76 percent / NaH, Bu₄N⁺Br^-

2: 95 percent / H₃O⁺

3: 98 percent / Et₃N

4: 98 percent / NaH, Bu₄N⁺I^-

5: 98 percent / Bu₄N⁺F^-

6: 90 percent / (COCl)2, Me₂SO, Et₃N

7: 1.) t-BuOK, 2.) MsCl

8: 60 percent

9: 74 percent / PhNCO, Et₃N / benzene / Heating

10: 67 percent / H₂ / Ni

11: 65 percent / LiAlH₄

12: 90 percent

13: 86 percent

14: 55 percent / NaOAc, HMPA / 96 h / 100 °C

15: 94 percent / camphorsulfonic acid / methanol / Ambient temperature

16: 80 percent

17: 85 percent / 0.5percent aq. H₂SO₄

18: 60 percent / NaBH₄

19: 70 percent / TsCl, pyridine

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; oxonium; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; phenyl isocyanate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; p-toluenesulfonyl chloride; nickel; In methanol; benzene;
DOI:10.1021/jo00209a050

Reference yield:

: 100-39-0
benzyl bromide

: 96212-59-8
2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 76 percent / NaH, Bu₄N⁺Br^-

2: 95 percent / H₃O⁺

3: 98 percent / Et₃N

4: 98 percent / NaH, Bu₄N⁺I^-

5: 98 percent / Bu₄N⁺F^-

6: 90 percent / (COCl)2, Me₂SO, Et₃N

7: 1.) t-BuOK, 2.) MsCl

8: 60 percent

9: 74 percent / PhNCO, Et₃N / benzene / Heating

10: 67 percent / H₂ / Ni

11: 65 percent / LiAlH₄

12: 90 percent

13: 86 percent

14: 55 percent / NaOAc, HMPA / 96 h / 100 °C

15: 94 percent / camphorsulfonic acid / methanol / Ambient temperature

16: 80 percent

17: 85 percent / 0.5percent aq. H₂SO₄

18: 60 percent / NaBH₄

19: 70 percent / TsCl, pyridine

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; oxonium; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; phenyl isocyanate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; p-toluenesulfonyl chloride; nickel; In methanol; benzene;
DOI:10.1021/jo00209a050