methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

Base Information

Chemical Name:methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate
CAS No.:844473-76-3
Molecular Formula:C₁₉H₂₆O₇
Molecular Weight:366.411
Hs Code.:

Synonyms:methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

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Chemical Property of methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

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Technology Process of methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

There total 8 articles about methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate 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: 60.0%

: 67-56-1
methanol

: 844473-75-2
(4R,4aR,6R,7S,7aS)-6-allyl-7-methoxymethoxy-2,2-dimethyl-4-phenyl-tetrahydrofuro[3,2-d][1,3]-dioxine

: 844473-76-3
methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

Guidance literature:: With potassium hydroxide; ozone; In dichloromethane; at -78 ℃;
DOI:10.1021/jo0483116

Reference yield:

: 677300-65-1
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

: 844473-76-3
methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / K₂CO₃ / methanol / 24 h / 20 °C

2: 85 percent / DIPEA / CH₂Cl₂ / 12 h / Heating

3: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5: 644 mg / diethyl ether / 1 h / -90 °C

6: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

7: 296 mg / TBAF / tetrahydrofuran / 24 h / 20 °C

8: 60 percent / O₃; KOH / CH₂Cl₂ / -78 °C

With pyridine; dmap; potassium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4: Swern oxidation;
DOI:10.1021/jo0483116

Reference yield:

: 1054634-48-8
(R)-[(4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-methoxymethoxy-acetaldehyde

: 844473-76-3
methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate

Guidance literature:: Multi-step reaction with 4 steps

1: 644 mg / diethyl ether / 1 h / -90 °C

2: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

3: 296 mg / TBAF / tetrahydrofuran / 24 h / 20 °C

4: 60 percent / O₃; KOH / CH₂Cl₂ / -78 °C

With dmap; potassium hydroxide; tetrabutyl ammonium fluoride; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo0483116