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

Base Information

Chemical Name:(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane
CAS No.:677300-67-3
Molecular Formula:C₂₇H₃₈O₆Si
Molecular Weight:486.681
Hs Code.:

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

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

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

There total 10 articles about (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-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: 72.0%

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

: 677300-67-3
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: With pyridine; hydrogen fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo0356356

Reference yield:

: 98-88-4
benzoyl chloride

: 677300-67-3
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: (Cyclohexyl)2BCl; Et₃N / diethyl ether / 1 h / 0 °C

2.2: diethyl ether / 5 h / -78 °C

3.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C

4.1: 80 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C

5.1: 72 percent / HF; pyridine / tetrahydrofuran / 20 °C

With pyridine; dmap; 3 A molecular sieve; camphor-10-sulfonic acid; dicyclohexylboron chloride; hydrogen fluoride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo0356356

Reference yield:

: 100-52-7
benzaldehyde

: 677300-67-3
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 4 steps

1.1: (Cyclohexyl)2BCl; Et₃N / diethyl ether / 1 h / 0 °C

1.2: diethyl ether / 5 h / -78 °C

2.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C

3.1: 80 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C

4.1: 72 percent / HF; pyridine / tetrahydrofuran / 20 °C

With pyridine; 3 A molecular sieve; camphor-10-sulfonic acid; dicyclohexylboron chloride; hydrogen fluoride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; acetone; acetonitrile;
DOI:10.1021/jo0356356