Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

Base Information

Chemical Name:Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester
CAS No.:213403-50-0
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

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Chemical Property of Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

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Technology Process of Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

There total 8 articles about Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl 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: 95.0%

: 108-24-7
acetic anhydride

: 213403-45-3
1-[(4R,5S,6R)-2-(4-Methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-yl]-butan-2-ol

: 213403-50-0
Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

Guidance literature:: With pyridine; dmap; for 17h; Ambient temperature;
DOI:10.1016/S0040-4039(98)01233-7

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 213403-50-0
Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / 10-camphorsulfonic acid / CH₂Cl₂; hexane / 14 h / 25 °C

2: 50 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 19 h / 25 °C

3: 95 percent / NaIO₄ / methanol; H₂O / 0.5 h / 25 °C

4: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

5: 69 percent / DDQ / CH₂Cl₂ / 1.5 h / 0 °C

6: 67 percent / NaBH₄ / methanol; H₂O / 2 h / 0 °C

7: 95 percent / 4-(dimethylamino)pyridine / pyridine / 17 h / 25 °C

With dmap; sodium tetrahydroborate; sodium periodate; AD-mix-α; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 2: Sharpless dihydroxylation / 4: Mukaiyama aldol reaction;
DOI:10.1021/jo001377q

Reference yield:

: 213403-25-9
(E)-(2R,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-hex-4-enal

: 213403-50-0
Acetic acid 1-[(4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-propenyl)-[1,3]dioxan-4-ylmethyl]-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

2: 69 percent / DDQ / CH₂Cl₂ / 1.5 h / 0 °C

3: 67 percent / NaBH₄ / methanol; H₂O / 2 h / 0 °C

4: 95 percent / 4-(dimethylamino)pyridine / pyridine / 17 h / 25 °C

With dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; methanol; dichloromethane; water; 1: Mukaiyama aldol reaction;
DOI:10.1021/jo001377q