5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide

Base Information

• Chemical Name: 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide
• CAS No.: 426824-57-9
• Molecular Formula: C₂₆H₄₁N₃O₇SSi
• Molecular Weight: 567.779
• Mol file: 426824-57-9.mol

Synonyms:5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide

Chemical Property of 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide

There total 1 articles about 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide 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: 47.0%

2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide (129378-52-5) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 5-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (426824-56-8) + 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (426824-57-9)

Guidance literature:

2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.25h;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In tetrahydrofuran; hexane; at -70 - 20 ℃; for 2.75h;

DOI:10.1016/S0040-4020(03)01055-X

Reference yield:

benzyl bromide (100-39-0) + 5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (426824-57-9) → 5-[(R)-Benzyloxy-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (426824-59-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(03)01055-X

Reference yield:

5-[(R)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (426824-57-9) → 4(5)-(2,3,4-tri-O-benzyl-α-D-arabinopyranosyl)-1H-imidazole (613234-45-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

2.1: 1.06 g / hydrochloric acid / H₂O; tetrahydrofuran / 1.5 h / Heating

3.1: 87 percent / NaBH₄ / methanol / 0 - 20 °C

4.1: 48 percent / 4-(dimethylamino)pyridine; pyridine / 48 h / 80 - 90 °C

5.1: 47 percent / NaH; n-BuN₄I / tetrahydrofuran; various solvent(s) / 0 - 20 °C

6.1: pyridine / -30 - 20 °C

7.1: pyridine / 60 - 80 °C

7.2: 36 mg / hydrochloric acid / H₂O; tetrahydrofuran / Heating

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)01055-X

upstream raw materials:

2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

5-[(R)-Benzyloxy-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methyl]-2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide

(6R,7S)-7,9-dibenzyloxy-6,7-dihydro-5H-imidazo[1,5-a]azepin-6-ol

1,3-di-O-benzyl-1-[1H-imidazol-4⁽⁵⁾-yl]-L-gulo-pentitol

1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4⁽⁵⁾-yl]-L-gulo-pentitol