N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

Base Information

Chemical Name:N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide
CAS No.:168072-76-2
Molecular Formula:C₂₁H₂₇NO₈
Molecular Weight:421.447
Hs Code.:

Synonyms:N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

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Chemical Property of N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

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Technology Process of N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

There total 21 articles about N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide 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: 87.0%

: Benzoyl-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

: 168072-76-2
N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

Guidance literature:: With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;
DOI:10.1016/0040-4039(95)00093-R

Reference yield:

: 152998-13-5
(S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-but-3-en-1-ol

: 168072-76-2
N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

Guidance literature:: Multi-step reaction with 21 steps

1: dimethylformamide / 23 °C

2: 1) ozone, 2) PPh₃ / 1) -78 deg C

3: TiCl₄

4: 1) BuLi / 1) THF, 0 deg C, 2) 23 deg C

5: 1) IBr, 2) NaOH (sat.) / 1) CH₂Cl₂, -78 deg C, 2) dioxane, H₂O, 23 deg C

6: NaOAc, H₂O / dimethylformamide / 65 °C

7: pyridine / CH₂Cl₂ / -78 °C

8: pyridine / CH₂Cl₂ / 0 °C

9: H₂O, AcOH / 80 °C

10: KIO₄ / tetrahydrofuran; H₂O

11: 93 percent / 4A mol sieves / toluene / -78 °C

12: 1) dimethyldioxirane, 2) AcOH / 1) acetone, 2) MeOH, 23 deg C

13: Ti(O-i-Pr)4, (-)-DIPT, TBHP / CH₂Cl₂ / -20 °C

14: Zn, AcOH / 50 °C

15: 87 percent / imidazol / toluene / 23 °C

16: 88 percent / P₂O₅ / 23 °C

17: TBAF, AcOH / tetrahydrofuran

18: CrO₃, H₂SO₄ / acetone / 0 - 5 °C

19: 1) (PhO)2P(O)N₃, Et₃N / 2) THF, 65 deg C

20: 1) LiHDMS / 1) THF, - 78 deg C, 1 h, 2) THF, -78 deg C to 0 deg C, 6 h

21: 87 percent / TBAF / dimethylformamide / 0.08 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; potassium metaperiodate; 4 A molecular sieve; sulfuric acid; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; sodium acetate; 3,3-dimethyldioxirane; phosphorus pentoxide; iodine(I) bromide; titanium tetrachloride; D-(-)-diisopropyl tartrate; ozone; acetic acid; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/0040-4039(95)00093-R

Reference yield:

: 152998-14-6
(R)-2,2-Diethyl-4-((S)-1-methoxy-2,2-dimethyl-but-3-enyl)-[1,3]dioxolane

: 168072-76-2
N-[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-benzamide

Guidance literature:: Multi-step reaction with 20 steps

1: 1) ozone, 2) PPh₃ / 1) -78 deg C

2: TiCl₄

3: 1) BuLi / 1) THF, 0 deg C, 2) 23 deg C

4: 1) IBr, 2) NaOH (sat.) / 1) CH₂Cl₂, -78 deg C, 2) dioxane, H₂O, 23 deg C

5: NaOAc, H₂O / dimethylformamide / 65 °C

6: pyridine / CH₂Cl₂ / -78 °C

7: pyridine / CH₂Cl₂ / 0 °C

8: H₂O, AcOH / 80 °C

9: KIO₄ / tetrahydrofuran; H₂O

10: 93 percent / 4A mol sieves / toluene / -78 °C

11: 1) dimethyldioxirane, 2) AcOH / 1) acetone, 2) MeOH, 23 deg C

12: Ti(O-i-Pr)4, (-)-DIPT, TBHP / CH₂Cl₂ / -20 °C

13: Zn, AcOH / 50 °C

14: 87 percent / imidazol / toluene / 23 °C

15: 88 percent / P₂O₅ / 23 °C

16: TBAF, AcOH / tetrahydrofuran

17: CrO₃, H₂SO₄ / acetone / 0 - 5 °C

18: 1) (PhO)2P(O)N₃, Et₃N / 2) THF, 65 deg C

19: 1) LiHDMS / 1) THF, - 78 deg C, 1 h, 2) THF, -78 deg C to 0 deg C, 6 h

20: 87 percent / TBAF / dimethylformamide / 0.08 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; potassium metaperiodate; 4 A molecular sieve; sulfuric acid; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; sodium acetate; 3,3-dimethyldioxirane; phosphorus pentoxide; iodine(I) bromide; titanium tetrachloride; D-(-)-diisopropyl tartrate; ozone; acetic acid; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/0040-4039(95)00093-R