2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester
CAS No.:571201-32-6
Molecular Formula:C₃₀H₄₀O₇
Molecular Weight:512.643
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

There total 7 articles about 2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl 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: 85.0%

: 100-39-0
benzyl bromide

: 571201-31-5
2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-hydroxy-5-{(R)-1-hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

: 571201-32-6
2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: benzyl bromide; 2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-hydroxy-5-{(R)-1-hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester; With tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; for 120h; Heating;

With IR resin (H+ form); In dichloromethane; for 1h; pH=1; Further stages.;
DOI:10.1002/ejoc.200390184

Reference yield:

: 10257-28-0
D-Galactose

: 571201-32-6
2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH; sodium iodide / various solvent(s) / 120 h / 20 °C

1.2: Pyr / various solvent(s) / 24 h / 0 °C

2.1: 2.01 g / MeONa / methanol

3.1: 75 percent / DMAP / pyridine / 2 h

4.1: 77 percent / triethylamine; DMAP / tetrahydrofuran / 1 h / 0 °C

5.1: TBAI; NaH / CH₂Cl₂ / 120 h / Heating

5.2: 85 percent / IR resin (H+ form) / CH₂Cl₂ / 1 h / pH 1

With dmap; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1002/ejoc.200390184

Reference yield:

: 3282-30-2
pivaloyl chloride

: 571201-32-6
2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 77 percent / triethylamine; DMAP / tetrahydrofuran / 1 h / 0 °C

2.1: TBAI; NaH / CH₂Cl₂ / 120 h / Heating

2.2: 85 percent / IR resin (H+ form) / CH₂Cl₂ / 1 h / pH 1

With dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.200390184