2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Base Information Edit

Chemical Name:2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
CAS No.:164217-32-7
Molecular Formula:C₂₀H₂₈O₆
Molecular Weight:364.439
Hs Code.:
Mol file:164217-32-7.mol

Synonyms:

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Chemical Property of 2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester Edit

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Technology Process of 2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-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:

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 3282-30-2
pivaloyl chloride

: 164217-32-7
2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃; for 15h;
DOI:10.1246/bcsj.67.3057

Reference yield:

: 164217-32-7
2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

: AB₃₂₁₇-A

Guidance literature:: Multi-step reaction with 11 steps

1: 50percent aq. acetic acid / 5 h / 100 °C

2: 94 percent / (n-Bu₃)P / tetrahydrofuran / 0.5 h / 25 °C

3: MeLi / diethyl ether / 0.25 h / 25 °C

4: imidazole / dimethylformamide / 0.5 h / 25 °C

5: tetrabutylammonium iodide, NaH / tetrahydrofuran / 2 h / 25 °C

6: (n-Bu₄)NF / tetrahydrofuran / 0.5 h / 25 °C

7: triethylamine / CH₂Cl₂ / 0.08 h / -78 °C

8: 1.) n-BuLi, MS 4A / 1.) DMF, hexane, 0 deg C, 5 min, 2.) DMF, 25 deg C, 0.5 h

9: 90 percent / dl-10-camphorosulfonic acid / methanol; dioxane / 2 h / 25 °C

10: 64 percent / NBS, MS₄AP / toluene / 24 h / 90 °C / var. solvents, temp., times

11: 80 percent / 0.01 M aq. HCl, H₂ / Pd(OH)2 / dioxane / 12 h / 25 °C / 760 Torr

With 1H-imidazole; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; tributylphosphine; DL-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; methyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1246/bcsj.67.3057