2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 88559-47-1
• Molecular Formula: C₃₂H₃₈O₆
• Molecular Weight: 518.65

Synonyms:2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 2 articles about 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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: 87.0%

pivaloyl chloride (3282-30-2) + 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol (84709-46-6) → 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (88559-47-1)

Guidance literature:

With pyridine; at 25 ℃; for 1h;

DOI:10.1016/S0040-4039(00)88259-3

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (88559-47-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; sodium tetrahydroborate; In ethanol;

DOI:10.1016/S0040-4039(00)88259-3

Reference yield: 84.0%

t-butyldimethylsiyl triflate (69739-34-0) + 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (88559-47-1) → 2,2-Dimethyl-propionic acid (4S,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (88559-48-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)88259-3

upstream raw materials:

pivaloyl chloride

2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

Downstream raw materials:

2,2-Dimethyl-propionic acid (4S,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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

{2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

{2-[(4R,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

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