methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

Base Information

Chemical Name:methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate
CAS No.:844473-79-6
Molecular Formula:C₃₁H₅₆O₈Si₂
Molecular Weight:612.952
Hs Code.:

methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

Synonyms:methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

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Chemical Property of methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

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Technology Process of methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

There total 8 articles about methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate 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

: 844473-78-5
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxymethoxy)pent-4-enyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

: 844473-79-6
methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

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

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 844473-79-6
methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 20 °C

2: 60 percent / O₃; KOH / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; potassium hydroxide; ozone; In dichloromethane;
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

: 844473-79-6
methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-4-(methoxymethoxy)butyrate

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: diethyl ether / 1 h / -90 °C

6: 96 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 20 °C

7: 60 percent / O₃; KOH / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; potassium hydroxide; oxalyl dichloride; 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