(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

Base Information

Chemical Name:(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone
CAS No.:154796-70-0
Molecular Formula:C₄₀H₄₉NO₇SSi
Molecular Weight:715.983
Hs Code.:

Synonyms:(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

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Chemical Property of (3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

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Technology Process of (3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

There total 9 articles about (3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone 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: 54.0%

: 20194-18-7
sodium phenyl-methanolate

: 154796-68-6
(4R,5R,6S,7S)-8-(O-tert-butyldiphenylsilyl)-4,5,6,7,8-pentahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-2(E)-octen-1-one

: (3R,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

: 154796-70-0
(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 5h;

Reference yield:

: 3292-77-1
2-bromo-1-thiazol-2-yl-ethanone

: 154796-70-0
(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / toluene / 3 h / Ambient temperature

2: 95 percent / 1N aq. NaOH / 0.5 h

3: 82 percent / 4A-molecular sieve / CHCl₃ / 14 h / Heating

4: 54 percent / tetrahydrofuran / 5 h / 0 °C

With sodium hydroxide; 4 A molecular sieve; In tetrahydrofuran; chloroform; toluene;

Reference yield:

: 3458-28-4
D-Mannose

: 154796-70-0
(3S,4R,5R,6S,7S)-3-O-benzyl-8-(O-tert-butyldiphenylsilyl)-3,4,5,6,7,8-hexahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

Guidance literature:: Multi-step reaction with 6 steps

1: conc. HCl / 0.25 h / Ambient temperature

2: TEA / dimethylformamide / 1 h / Ambient temperature

3: 10-camphorsulphonic acid (CSA) / 6 h / Ambient temperature

4: 95 percent / H₂O, HgO, HgCl₂ / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

5: 82 percent / 4A-molecular sieve / CHCl₃ / 14 h / Heating

6: 54 percent / tetrahydrofuran / 5 h / 0 °C

With hydrogenchloride; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; water; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;