(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester
• CAS No.: 562823-70-5
• Molecular Formula: C₂₆H₃₆O₅Si
• Molecular Weight: 456.654

Synonyms:(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Chemical Property of (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

There total 2 articles about (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 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: 92.0%

2,2-dimethoxy-propane (77-76-9) + (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester (562823-69-2) → (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (562823-70-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In acetone; at 23 ℃; for 5h;

DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate (256494-25-4) → (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (562823-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

2: 92 percent / PPTS / acetone / 5 h / 23 °C

With AD-mix-α; methanesulfonamide; pyridinium p-toluenesulfonate; In water; acetone; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)00744-5

Reference yield: 97.0%

(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (562823-70-5) → {(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol (562823-56-7)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(03)00744-5

upstream raw materials:

2,2-dimethoxy-propane

(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate

Downstream raw materials:

{(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

2-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol

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