Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
CAS No.:185994-25-6
Molecular Formula:C₅₇H₅₄O₈SSi
Molecular Weight:927.202
Hs Code.:

Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Synonyms:Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl 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: 93.0%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: Benzoic acid (2S,3R,4S,5S,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

: 185994-25-6
Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; at 25 ℃; for 1h;
DOI:10.1021/ja963482g

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 185994-25-6
Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / (+/-)-10-camphorsulfonic acid / benzene / 12 h / Heating

2: 88 percent / imidazole / dimethylformamide / 12 h / 0 °C

3: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h

4: BH₃*Me₃N; AlCl₃; 4 Angstroem MS / CH₂Cl₂; diethyl ether / 5 h / 0 °C

5: HCl / methanol / 3 h / 25 °C

6: 96 percent / imidazole / dimethylformamide / 3 h / 25 °C

7: 93 percent / pyridine / 1 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; aluminium trichloride; trimethylamine-borane; 4 Angstroem MS; camphor-10-sulfonic acid; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Cyclization / 2: silylation / 3: Acylation / 4: Reduction / 5: desilylation / 6: silylation / 7: alkoxycarbonylation;
DOI:10.1021/ja963482g

Reference yield:

: 108-98-5
thiophenol

: 185994-25-6
Benzoic acid (2S,3R,4S,5R,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 82 percent / SnCl₄ / CH₂Cl₂ / 4 h / 0 °C

2: 98 percent / K₂CO₃ / tetrahydrofuran; methanol / 15 h / 25 °C

3: 96 percent / (+/-)-10-camphorsulfonic acid / benzene / 12 h / Heating

4: 88 percent / imidazole / dimethylformamide / 12 h / 0 °C

5: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h

6: BH₃*Me₃N; AlCl₃; 4 Angstroem MS / CH₂Cl₂; diethyl ether / 5 h / 0 °C

7: HCl / methanol / 3 h / 25 °C

8: 96 percent / imidazole / dimethylformamide / 3 h / 25 °C

9: 93 percent / pyridine / 1 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; aluminium trichloride; trimethylamine-borane; 4 Angstroem MS; camphor-10-sulfonic acid; tin(IV) chloride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Substitution / 2: deacetylation / 3: Cyclization / 4: silylation / 5: Acylation / 6: Reduction / 7: desilylation / 8: silylation / 9: alkoxycarbonylation;
DOI:10.1021/ja963482g