(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

Base Information

Chemical Name:(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester
CAS No.:88559-52-8
Molecular Formula:C₃₆H₅₁O₈PSi
Molecular Weight:670.855
Hs Code.:

(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

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Chemical Property of (2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

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Technology Process of (2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

There total 7 articles about (2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl 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: 64.0%

: 34939-91-8,58648-56-9
dimethyl lithiomethylphosphonate

: 88559-50-6
(4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 88559-52-8,88588-69-6
(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)88259-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 88559-52-8,88588-69-6
(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 83 percent / n-butyllithium / tetrahydrofuran / 1 h / 0 °C

3: 67 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 18 h / 25 °C

4: 64 percent / tetrahydrofuran / 0.5 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; 4 A molecular sieve; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)88259-3

Reference yield:

: 54503-64-9,54503-65-0
2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

: 88559-52-8,88588-69-6
(2-{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-hydroxy-ethyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 72 percent / sodium borohydride / ethanol / 1 h / 0 °C

2: 87 percent / pyridine / 1 h / 25 °C

3: 84 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4: 83 percent / n-butyllithium / tetrahydrofuran / 1 h / 0 °C

5: 67 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 18 h / 25 °C

6: 64 percent / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)88259-3