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

Base Information

• Chemical Name: 1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4⁽⁵⁾-yl]-L-gulo-pentitol
• CAS No.: 426824-67-1
• Molecular Formula: C₃₆H₃₈N₂O₉S₂
• Molecular Weight: 706.838

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

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

Chemical Property:

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

There total 10 articles about 1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4⁽⁵⁾-yl]-L-gulo-pentitol 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: 34.0%

1,3-di-O-benzyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)-5-O-triphenylmethyl-L-gulo-pentitol (613234-38-1) + benzenesulfonyl chloride (1939-99-7) → 6,8-di-O-benzyl-7-O-phenylmethanesulphonyl-imidazolo[1,5]-D-manno-piperidinose (426824-68-2) + 1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4(5)-yl]-L-gulo-pentitol (426824-67-1)

Guidance literature:

1,3-di-O-benzyl-1-(1-triphenylmethyl-1H-imidazol-4-yl)-5-O-triphenylmethyl-L-gulo-pentitol; benzenesulfonyl chloride; With pyridine; at -30 - 20 ℃;

With hydrogenchloride; In tetrahydrofuran; water; for 1.25h; Heating;

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

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4(5)-yl]-L-gulo-pentitol (426824-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -70 °C

1.2: 47 percent / hexane; tetrahydrofuran / 2.75 h / -70 - 20 °C

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

3.1: 1.06 g / hydrochloric acid / H₂O; tetrahydrofuran / 1.5 h / Heating

4.1: 87 percent / NaBH₄ / methanol / 0 - 20 °C

5.1: 48 percent / 4-(dimethylamino)pyridine; pyridine / 48 h / 80 - 90 °C

6.1: pyridine / -30 - 20 °C

6.2: 34 percent / hydrochloric acid / tetrahydrofuran; H₂O / 1.25 h / Heating

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; sodium hydride; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide;

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

Reference yield:

(5R)-3,5-di-O-benzyl-5-[1H-imidazol-4(5)-yl]-D-xylofuranose → 1,3-di-O-benzyl-2,4-di-O-phenylmethanesulphonyl-1-[1H-imidazol-4(5)-yl]-L-gulo-pentitol (426824-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / NaBH₄ / methanol / 0 - 20 °C

2.1: 48 percent / 4-(dimethylamino)pyridine; pyridine / 48 h / 80 - 90 °C

3.1: pyridine / -30 - 20 °C

3.2: 34 percent / hydrochloric acid / tetrahydrofuran; H₂O / 1.25 h / Heating

With pyridine; dmap; sodium tetrahydroborate; In methanol;

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

upstream raw materials:

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

benzenesulfonyl chloride

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

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

Downstream raw materials:

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

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