2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester
CAS No.:863660-55-3
Molecular Formula:C₄₁H₆₅NO₇S₂Si₂
Molecular Weight:804.273
Hs Code.:

2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Synonyms:2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of 2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of 2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

There total 25 articles about 2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl 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%

: 863663-07-4
2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazol-2-ylsulfanyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

: 863660-55-3
2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With ammonium molybdate(VI) tetrahydrate; dihydrogen peroxide; In ethanol; water; at 20 ℃; for 12h;
DOI:10.1021/jo0507993

Reference yield:

: 677707-78-7
2-((2R,6S)-6-Methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-2-methyl-propionic acid methyl ester

: 863660-55-3
2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / KOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

2.1: 97 percent / BH₃*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C

3.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

4.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C

4.2: 92 percent / NaOH; H₂O₂ / tetrahydrofuran / 0.17 h / 20 °C

5.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

6.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating

7.1: OsO₄; 4-methylmorpholine N-oxide / H₂O; acetone / 20 °C

7.2: 89 percent / NaIO₄ / H₂O; acetone / 0.5 h / 20 °C

8.1: KO-t-Bu; n-BuLi; B(^dIpc)2OMe / tetrahydrofuran / -78 - -45 °C

8.2: 82 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

10.1: 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 24 h / 20 °C

10.2: 93 percent / NaIO₄ / acetone; H₂O / 0.5 h

11.1: 99 percent / NaBH₄ / ethanol / 0.5 h / 20 °C

12.1: 100 percent / Ph₃P; DIAD / tetrahydrofuran / 1 h / 0 °C

13.1: 90 percent / ammonium molybdate tetrahydrate; H₂O₂ / ethanol; H₂O / 12 h / 20 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; ammonium molybdate(VI) tetrahydrate; Trimethyl borate; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; B(^dIpc)2OMe; sulfur trioxide; potassium tert-butylate; dihydrogen peroxide; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; triphenylphosphine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 4.1: Brown allylation / 8.1: Brown crotylation;
DOI:10.1021/jo0507993

Reference yield:

: 863659-93-2
(R)-6-Iodo-3-((E)-2-methoxycarbonyl-vinyloxy)-2,2-dimethyl-hexanoic acid methyl ester

: 863660-55-3
2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 99 percent / hypophosphorous acid; 1-ethylpiperidine; Et₃B / ethanol / 0.5 h / 20 °C

2.1: 100 percent / KOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

3.1: 97 percent / BH₃*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C

4.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

5.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C

5.2: 92 percent / NaOH; H₂O₂ / tetrahydrofuran / 0.17 h / 20 °C

6.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

7.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating

8.1: OsO₄; 4-methylmorpholine N-oxide / H₂O; acetone / 20 °C

8.2: 89 percent / NaIO₄ / H₂O; acetone / 0.5 h / 20 °C

9.1: KO-t-Bu; n-BuLi; B(^dIpc)2OMe / tetrahydrofuran / -78 - -45 °C

9.2: 82 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

11.1: 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 24 h / 20 °C

11.2: 93 percent / NaIO₄ / acetone; H₂O / 0.5 h

12.1: 99 percent / NaBH₄ / ethanol / 0.5 h / 20 °C

13.1: 100 percent / Ph₃P; DIAD / tetrahydrofuran / 1 h / 0 °C

14.1: 90 percent / ammonium molybdate tetrahydrate; H₂O₂ / ethanol; H₂O / 12 h / 20 °C

With 1-ethyl-piperidine; pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; ammonium molybdate(VI) tetrahydrate; Trimethyl borate; triethyl borane; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; B(^dIpc)2OMe; sulfur trioxide; potassium tert-butylate; dihydrogen peroxide; hypophosphorous acid; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; triphenylphosphine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 5.1: Brown allylation / 9.1: Brown crotylation;
DOI:10.1021/jo0507993