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

Base Information

Chemical Name:(4R,4aR,6R,7S,7aS)-6-allyl-7-methoxymethoxy-2,2-dimethyl-4-phenyl-tetrahydrofuro[3,2-d][1,3]-dioxine
CAS No.:844473-75-2
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,4aR,6R,7S,7aS)-6-allyl-7-methoxymethoxy-2,2-dimethyl-4-phenyl-tetrahydrofuro[3,2-d][1,3]-dioxine

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Technology Process of (4R,4aR,6R,7S,7aS)-6-allyl-7-methoxymethoxy-2,2-dimethyl-4-phenyl-tetrahydrofuro[3,2-d][1,3]-dioxine

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

: 1054314-09-8
Methanesulfonic acid (S)-1-{(R)-[(4R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-methoxymethoxy-methyl}-but-3-enyl ester

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;
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

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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; pyridine hydrogenfluoride; 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

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

Guidance literature:: Multi-step reaction with 3 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

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