(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Base Information

Chemical Name:(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane
CAS No.:677300-85-5
Molecular Formula:C₂₀H₃₄O₅Si
Molecular Weight:382.572
Hs Code.:

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

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Chemical Property of (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

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Technology Process of (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

There total 3 articles about (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane 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: 84.0%

: 677300-81-1
(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

: 677300-85-5
(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1021/jo0356356

Reference yield:

: (1S,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-4-phenylbutyl benzoate

: 677300-85-5
(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C

2: 73 percent / HF; pyridine / tetrahydrofuran / 20 °C

3: 84 percent / K₂CO₃ / methanol / 1 h / 20 °C

With pyridine; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; potassium carbonate; In tetrahydrofuran; methanol; acetone;
DOI:10.1021/jo0356356

Reference yield:

: 677300-79-7
(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

: 677300-85-5
(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / HF; pyridine / tetrahydrofuran / 20 °C

2: 84 percent / K₂CO₃ / methanol / 1 h / 20 °C

With pyridine; hydrogen fluoride; potassium carbonate; In tetrahydrofuran; methanol;
DOI:10.1021/jo0356356