20-O-Methyl-23-O-trityltylonolide Hemiacetal

Base Information

Chemical Name:20-O-Methyl-23-O-trityltylonolide Hemiacetal
CAS No.:81132-63-0
Molecular Formula:C₄₃H₅₂O₇
Molecular Weight:680.882
Hs Code.:

Synonyms:20-O-Methyl-23-O-trityltylonolide Hemiacetal

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Chemical Property of 20-O-Methyl-23-O-trityltylonolide Hemiacetal

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Technology Process of 20-O-Methyl-23-O-trityltylonolide Hemiacetal

There total 41 articles about 20-O-Methyl-23-O-trityltylonolide Hemiacetal 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: 86.0%

: 81114-73-0,81132-62-9,81600-33-1,81600-34-2,84710-26-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

: 81114-52-5,81132-63-0,84171-61-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Guidance literature:: With chromium(VI) oxide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 20h;
DOI:10.1016/S0040-4039(01)82047-5

Reference yield:

: 78785-21-4
3,5-Didesoxy-1,2-O-isopropyliden-3-C-methyl-α-D-xylo-hexofuranose

: 81114-52-5,81132-63-0,84171-61-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Guidance literature:: Multi-step reaction with 20 steps

1: NaH / dimethylformamide / 1 h / 20 °C

2: H₂O, H₂SO₄ / 2-methyl-propan-2-ol / 50 °C

3: toluene / 18 h / 50 °C

4: TsOH / dimethylformamide / 1 h / 20 °C

5: BuLi / 2.5 h / -78 °C

6: BF₃ - Et₂O / 18 h / 20 °C

7: DIBAL / toluene / 0.5 h / -78 °C

8: Amberlyst 15 (H type) / 2 h / 20 °C

9: NaH / dimethylformamide / 4 h / 20 °C

10: 85 percent / CdCO₃, HgCl₂ / acetone; H₂O / 1 h / 20 °C

11: 90 percent / toluene / 90 h / 60 °C

12: H₂ / Pd-black / methanol / 20 °C / 2280 Torr

13: O₂ / Pt-black, NaHCO₃ / H₂O / 80 °C

14: 52 percent / diethyl ether / 20 °C

15: 41 percent / LDA / tetrahydrofuran / 2 h / -78 - 0 °C

16: NaBH₄ / methanol / 0 °C

17: 85 percent / H₂O, KOH / methanol / 15 h / 60 °C

18: Ph₃P / 20 °C

19: toluene / 20 h / 110 °C

20: 86 percent / CrO₃ / hexamethylphosphoric acid triamide / 20 h / 20 °C

With chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; Amberlyst 15 (H type); sulfuric acid; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; sodium hydrogencarbonate; palladium; platinum; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)82047-5

Reference yield:

: 81114-51-4
((3aR,5R,6S,6aR)-2,2,6-Trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde

: 81114-52-5,81132-63-0,84171-61-9
(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Guidance literature:: Multi-step reaction with 21 steps

1: NaBH₄ / methanol / 20 °C

2: NaH / dimethylformamide / 1 h / 20 °C

3: H₂O, H₂SO₄ / 2-methyl-propan-2-ol / 50 °C

4: toluene / 18 h / 50 °C

5: TsOH / dimethylformamide / 1 h / 20 °C

6: BuLi / 2.5 h / -78 °C

7: BF₃ - Et₂O / 18 h / 20 °C

8: DIBAL / toluene / 0.5 h / -78 °C

9: Amberlyst 15 (H type) / 2 h / 20 °C

10: NaH / dimethylformamide / 4 h / 20 °C

11: 85 percent / CdCO₃, HgCl₂ / acetone; H₂O / 1 h / 20 °C

12: 90 percent / toluene / 90 h / 60 °C

13: H₂ / Pd-black / methanol / 20 °C / 2280 Torr

14: O₂ / Pt-black, NaHCO₃ / H₂O / 80 °C

15: 52 percent / diethyl ether / 20 °C

16: 41 percent / LDA / tetrahydrofuran / 2 h / -78 - 0 °C

17: NaBH₄ / methanol / 0 °C

18: 85 percent / H₂O, KOH / methanol / 15 h / 60 °C

19: Ph₃P / 20 °C

20: toluene / 20 h / 110 °C

21: 86 percent / CrO₃ / hexamethylphosphoric acid triamide / 20 h / 20 °C

With chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; Amberlyst 15 (H type); sulfuric acid; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; sodium hydrogencarbonate; palladium; platinum; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)82047-5