(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

Base Information

Chemical Name:(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal
CAS No.:133839-46-0
Molecular Formula:C₂₅H₃₈O₆
Molecular Weight:434.573
Hs Code.:

Synonyms:(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

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Chemical Property of (2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

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Technology Process of (2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

There total 22 articles about (2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal 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: 91.0%

: 129250-98-2
(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenol

: 133839-46-0
(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane;

Reference yield:

: 120400-68-2
(R)-1-{(3aR,5S,6R,6aR)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl}-ethane-1,2-diol

: 133839-46-0
(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

Guidance literature:: Multi-step reaction with 17 steps

1: imidazole / CH₂Cl₂ / 1 h / ice-bath

2: 97.9 percent / pyridine / 6 h / Ambient temperature

3: 91 percent / 1N HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

5: 1) NaH / 1) DMF, r.t., 30 min, 2) 60 deg C, 90 min

6: 1) NaH / 1) THF, DMSO, r.t., 2h, 2) 12h

7: 3N H₂SO₄ / dioxane / 48 h / Ambient temperature

8: NaIO₄ / H₂O; methanol / 2 h / 5 °C

10: 1) DIBAH, 2) CSA / 1) CH₂Cl₂, hexane, -80 deg C, 1h, 2) r.t., 1h

11: 77.8 percent / H₂ / Raney-Ni W-2 / ethanol / 9 h / 760 Torr / Ambient temperature

12: 1) (COCl₂)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -90 deg C, 30 min, 2) -90 to -70 deg C, 1h

13: 1) MgBr₂*Et₂O / 1) CH₂Cl₂, Et₂O, -60 deg C, 10 min, 2) <60 deg C, 15 min

14: 80 percent / 1N HCl / tetrahydrofuran / 6 h / 50 °C

15: 91 percent / Ca(BH₄)2 / ethanol / 3 h / Ambient temperature

16: 90 percent / CSA / benzene / 2 h / Ambient temperature

17: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -65 deg C, 30 min 2) a) -65 deg C, 30 min, b) to -30 deg C

With pyridine; 1H-imidazole; hydrogenchloride; sodium periodate; calcium borohydride; oxalyl dichloride; (COCl₂)2; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; magnesium bromide; Raney-Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; benzene;
DOI:10.1248/cpb.39.64

Reference yield:

: 129272-55-5
(3aR,5S,6R,6aR)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-5-(S)-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 133839-46-0
(2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenal

Guidance literature:: Multi-step reaction with 13 steps

1: 1) NaH / 1) DMF, r.t., 30 min, 2) 60 deg C, 90 min

2: 1) NaH / 1) THF, DMSO, r.t., 2h, 2) 12h

3: 3N H₂SO₄ / dioxane / 48 h / Ambient temperature

4: NaIO₄ / H₂O; methanol / 2 h / 5 °C

6: 1) DIBAH, 2) CSA / 1) CH₂Cl₂, hexane, -80 deg C, 1h, 2) r.t., 1h

7: 77.8 percent / H₂ / Raney-Ni W-2 / ethanol / 9 h / 760 Torr / Ambient temperature

8: 1) (COCl₂)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -90 deg C, 30 min, 2) -90 to -70 deg C, 1h

9: 1) MgBr₂*Et₂O / 1) CH₂Cl₂, Et₂O, -60 deg C, 10 min, 2) <60 deg C, 15 min

10: 80 percent / 1N HCl / tetrahydrofuran / 6 h / 50 °C

11: 91 percent / Ca(BH₄)2 / ethanol / 3 h / Ambient temperature

12: 90 percent / CSA / benzene / 2 h / Ambient temperature

13: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -65 deg C, 30 min 2) a) -65 deg C, 30 min, b) to -30 deg C

With hydrogenchloride; sodium periodate; calcium borohydride; oxalyl dichloride; (COCl₂)2; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide; Raney-Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; benzene;
DOI:10.1248/cpb.39.64