(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

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Chemical Name:(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol
CAS No.:470470-75-8
Molecular Formula:C₄₆H₇₈O₉Si₂
Molecular Weight:831.291
Hs Code.:

(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

Synonyms:(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

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Chemical Property of (2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

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Technology Process of (2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

There total 18 articles about (2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol 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: 55.0%

: 470470-74-7
(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane

: 470470-75-8
(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; sodium carbonate; In water; acetone; butan-1-ol; at 20 ℃; for 18h;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 470470-75-8
(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 17 steps

1.1: 98 percent / TFA / CH₂Cl₂ / 15 h / 20 °C

2.1: 88 percent / DIBAL-H / tetrahydrofuran / 5 h / -35 °C

3.1: 82 percent / n-BuLi / tetrahydrofuran / 18 h / -78 - 20 °C

4.1: 97 percent / imid.; DMAP; TBAI / 0.5 h / 20 °C

5.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

5.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

7.1: 49 percent / LDA / 0.03 h / -78 °C

8.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

9.1: 74 percent / PPTS / 18 h / 20 °C

10.1: 95 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

11.1: 100 percent / (COCl)2; DMSO; Et₃N / -78 °C

12.1: 100 percent / tetrahydrofuran / -78 - 20 °C

13.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

14.1: 55 percent / ZnI₂; 4 Angstroem MS / CH₂Cl₂ / 18 h / 20 °C / protect from light

15.1: HF / H₂O; acetonitrile / 24 h / 20 °C

15.2: 34 percent / PPTS / methanol / 3 h / 20 °C

16.1: 100 percent / imid.; TBAI; DMAP / CH₂Cl₂ / 20 °C

17.1: 55 percent / Na₂CO₃; OsO₄; NMO / acetone; butan-1-ol; H₂O / 18 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; 4 Angstroem MS; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; zinc(II) iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone; acetonitrile; butan-1-ol;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 470470-75-8
(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / imid.; DMAP; TBAI / 0.5 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

2.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 49 percent / LDA / 0.03 h / -78 °C

5.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

6.1: 74 percent / PPTS / 18 h / 20 °C

7.1: 95 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

8.1: 100 percent / (COCl)2; DMSO; Et₃N / -78 °C

9.1: 100 percent / tetrahydrofuran / -78 - 20 °C

10.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

11.1: 55 percent / ZnI₂; 4 Angstroem MS / CH₂Cl₂ / 18 h / 20 °C / protect from light

12.1: HF / H₂O; acetonitrile / 24 h / 20 °C

12.2: 34 percent / PPTS / methanol / 3 h / 20 °C

13.1: 100 percent / imid.; TBAI; DMAP / CH₂Cl₂ / 20 °C

14.1: 55 percent / Na₂CO₃; OsO₄; NMO / acetone; butan-1-ol; H₂O / 18 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 4 Angstroem MS; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; zinc(II) iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone; acetonitrile; butan-1-ol;
DOI:10.1016/S0040-4039(02)01054-7