(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

Base Information

Chemical Name:(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester
CAS No.:167964-38-7
Molecular Formula:C₁₇H₁₈O₁₁
Molecular Weight:398.323
Hs Code.:

Synonyms:(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

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Chemical Property of (1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

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Technology Process of (1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

There total 10 articles about (1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl 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: 90.0%

: (6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester 3,5-dimethyl ester

: 167964-38-7
(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 22 ℃; for 19h;

Reference yield:

: 167964-37-6
(7S)-2,7-Anhydro-8-deoxy-4-C-(methoxycarbonyl)-3-C-<(phenylmethoxy)carbonyl>-L-glycero-D-altro-7-octulo-7,4-furanosonic acid methyl ester

: 167964-38-7
(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 19h; Yield given;

Reference yield:

: 167964-31-0
(4R,5R,8R,9S)-9-Hydroxy-8,9-bis(hydroxymethyl)-2,2-dimethyl-4-<<<2-(trimethylsilyl)ethoxy>methoxy>methyl>-1,3,7-trioxaspiro<4.4>nonan-6-one

: 167964-38-7
(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4-benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 40 h / 25 °C

3: 2.) pyridine, p-TosOH / 1.) 90 deg C, 1h, 2.) CH₂Cl₂, MeOH, 25 deg C, 5 min

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

5: 1.) BuLi / 1.) THF, -23 deg C, 1.5 h, 2.) THF, -78 deg C, 1 h

6: 76 percent / 2percent HCl / methanol / 0.17 h / 25 °C

7: 73 percent / Hg(ClO₄)2, CaCO₃, H₂O / tetrahydrofuran / 2 h / 25 °C

8: 56 percent / 2percent HCl / 10 h / 60 °C

9: LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; n-butyllithium; mercury(II) perchlorate; water; Dess-Martin periodane; toluene-4-sulfonic acid; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;