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

Base Information

• Chemical Name: (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[1,3]dioxane
• CAS No.: 677300-80-0
• Molecular Formula: C₂₄H₄₀O₆Si
• Molecular Weight: 452.663

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

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

Chemical Property:

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

There total 2 articles about (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[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: 79.0%

(4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[1,3]dioxane (677300-78-6) → (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[1,3]dioxane (677300-80-0)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo0356356

Reference yield:

(1S,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate → (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[1,3]dioxane (677300-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C

2: 79 percent / HF; pyridine / tetrahydrofuran / 20 °C

With pyridine; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; In tetrahydrofuran; acetone;

DOI:10.1021/jo0356356

Reference yield:

methanesulfonyl chloride (124-63-0) + (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-hydroxy-1-benzoyloxyethyl]-6-isopropyl-2,2-dimethyl-[1,3]dioxane (677300-80-0) → Benzoic acid (S)-1-[(4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-isopropyl-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methanesulfonyloxy-ethyl ester

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo0356356

upstream raw materials:

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

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