2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester
• CAS No.: 632357-43-8
• Molecular Formula: C₂₅H₃₈O₆
• Molecular Weight: 434.573

Synonyms:2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester

There total 22 articles about 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl 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: 97.0%

2,2-dimethoxy-propane (77-76-9) + 2,2-Dimethyl-propionic acid 2-((2S,3R,4R,6S)-6-benzyloxymethyl-4-hydroxy-3-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-ethyl ester (632357-73-4) → 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester (632357-43-8)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 2h;

DOI:10.1021/jo034930n

Reference yield:

ethyl (S)-4-benzyloxy-3-hydroxybutanoate (112348-04-6) → 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester (632357-43-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: Me₃Al / tetrahydrofuran / 0.5 h / 20 °C

1.2: 92 percent / tetrahydrofuran / -10 - 20 °C

2.1: Mg / tetrahydrofuran / 1 h

2.2: 62 percent / tetrahydrofuran / 2 h / 20 °C

3.1: 97 percent / Et₃B; NaBH₄ / tetrahydrofuran; methanol; hexane / 5 h / -78 °C

4.1: camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

5.1: 2.092 g / DIBAL / CH₂Cl₂; cyclohexane / 5 h / 20 °C

6.1: N-methylmorpholine / acetonitrile / 48 h

7.1: 0.516 g / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

8.1: Et₃N; DMAP / benzene / 0.5 h / 20 °C

9.1: 4.143 g / n-Bu₃SnH; AIBN / benzene / 5 h / Heating

10.1: LiBH₄ / diethyl ether; tetrahydrofuran / 6 h / 20 °C

11.1: 4.233 g / pyridine; DMAP / CH₂Cl₂ / 8 h / 20 °C

12.1: 82 percent / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 36 h / 20 °C

13.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 8 h / 20 °C

14.1: 98 percent / camphorsulfonic acid / methanol / 1.5 h / 0 °C

15.1: 2-nitrophenyl selenocyanate; n-Bu₃P / tetrahydrofuran / 1 h / 20 °C

15.2: 92 percent / aq. H₂O₂ / CH₂Cl₂ / 5 h / 20 °C

16.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

16.2: NaIO₄ / ethanol; H₂O / 5 h / 20 °C

16.3: 92 percent / NaBH₄ / ethanol; H₂O / 0.17 h / 0 °C

17.1: 93 percent / aq. HCl / methanol / 5 h / 20 °C

18.1: 97 percent / camphorsulfonic acid / acetone / 2 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; potassium fluoride; sodium tetrahydroborate; osmium(VIII) oxide; lithium borohydride; ortho-nitrophenyl selenocyanate; 2,2'-azobis(isobutyronitrile); triethyl borane; tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; magnesium; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; water; acetone; acetonitrile; benzene; 12.1: Tamao oxidation;

DOI:10.1021/jo034930n

Reference yield:

(2S,4R)-1-Benzyloxy-5-methyl-hex-5-ene-2,4-diol (632357-74-5) → 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester (632357-43-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

2.1: 2.092 g / DIBAL / CH₂Cl₂; cyclohexane / 5 h / 20 °C

3.1: N-methylmorpholine / acetonitrile / 48 h

4.1: 0.516 g / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

5.1: Et₃N; DMAP / benzene / 0.5 h / 20 °C

6.1: 4.143 g / n-Bu₃SnH; AIBN / benzene / 5 h / Heating

7.1: LiBH₄ / diethyl ether; tetrahydrofuran / 6 h / 20 °C

8.1: 4.233 g / pyridine; DMAP / CH₂Cl₂ / 8 h / 20 °C

9.1: 82 percent / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 36 h / 20 °C

10.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 8 h / 20 °C

11.1: 98 percent / camphorsulfonic acid / methanol / 1.5 h / 0 °C

12.1: 2-nitrophenyl selenocyanate; n-Bu₃P / tetrahydrofuran / 1 h / 20 °C

12.2: 92 percent / aq. H₂O₂ / CH₂Cl₂ / 5 h / 20 °C

13.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

13.2: NaIO₄ / ethanol; H₂O / 5 h / 20 °C

13.3: 92 percent / NaBH₄ / ethanol; H₂O / 0.17 h / 0 °C

14.1: 93 percent / aq. HCl / methanol / 5 h / 20 °C

15.1: 97 percent / camphorsulfonic acid / acetone / 2 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; potassium fluoride; osmium(VIII) oxide; lithium borohydride; ortho-nitrophenyl selenocyanate; 2,2'-azobis(isobutyronitrile); tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; acetone; acetonitrile; benzene; 9.1: Tamao oxidation;

DOI:10.1021/jo034930n

upstream raw materials:

2,2-dimethoxy-propane

2,2-Dimethyl-propionic acid 2-((2S,3R,4R,6S)-6-benzyloxymethyl-4-hydroxy-3-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-ethyl ester

ethyl (S)-4-benzyloxy-3-hydroxybutanoate

(3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N-methylbutanamide

Downstream raw materials:

2,2-Dimethyl-propionic acid 2-{(4aS,5S,7S,8aR)-7-[(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-1-enyl]-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl}-ethyl ester

2,2-Dimethyl-propionic acid 2-{(4aS,5S,7S,8aR)-2,2,4a-trimethyl-7-[(E)-4-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-but-1-enyl]-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl}-ethyl ester

2,2-Dimethyl-propionic acid 2-{(4aS,5S,7S,8aR)-2,2,4a-trimethyl-7-[(E)-4-(1-phenyl-1H-tetrazole-5-sulfonyl)-but-1-enyl]-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl}-ethyl ester

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