(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran
CAS No.:724765-24-6
Molecular Formula:C₃₅H₆₂O₅Si₂
Molecular Weight:619.045
Hs Code.:

(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

Synonyms:(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

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Chemical Property of (2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

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Technology Process of (2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

There total 19 articles about (2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 724765-23-5
(2R,4S,5R,6S)-6-Allyl-2-((S)-5-benzyloxy-2-hydroxy-pentyl)-2-methoxy-5-vinyl-tetrahydro-pyran-4-ol

: 724765-24-6
(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 23 ℃; for 13h;
DOI:10.1002/anie.200453697

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 724765-24-6
(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 11 steps

1.1: tetrahydrofuran / 2 h / -90 °C

2.1: aq. H₂O₂; NaOH / tetrahydrofuran; methanol / 10 h / -90 - 23 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 97 percent / NaBH₄ / CH₂Cl₂; methanol / 1.5 h / -78 - 23 °C

4.1: TEMPO; aq. KBr; NaOCl / NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

5.1: 18-crown-6; TMSCN / CH₂Cl₂ / 1 h / 23 °C

5.2: 1.14 g / pyridinium p-toluenesulfonate / CH₂Cl₂; methanol / 5 h / 23 °C

6.1: 88 percent / pyridinium p-toluenesulfonate / acetone / 19 h / 68 °C

7.1: 92 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.5 h / -40 °C

8.1: Dowex 50X₂-100 ion-exchange resin; H₂O / methanol / 12 h / 23 °C

9.1: 0.74 g / Et₃N / methanol / 23 °C

10.1: 89 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 23 °C

11.1: 97 percent / imidazole; DMAP / dimethylformamide / 13 h / 23 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; 18-crown-6 ether; trimethylsilyl cyanide; Dowex 50X₂-100 ion-exchange resin; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; ozone; triethylamine; potassium bromide; lithium diisopropyl amide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/anie.200453697

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 724765-24-6
(2R,4S,5S,6S)-6-Allyl-2-[(S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-pentyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 12 steps

1.1: 93 percent / TEMPO; aq. KBr; NaOCl / NaHCO₃ / CH₂Cl₂ / cooling

2.1: tetrahydrofuran / 2 h / -90 °C

3.1: aq. H₂O₂; NaOH / tetrahydrofuran; methanol / 10 h / -90 - 23 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 97 percent / NaBH₄ / CH₂Cl₂; methanol / 1.5 h / -78 - 23 °C

5.1: TEMPO; aq. KBr; NaOCl / NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

6.1: 18-crown-6; TMSCN / CH₂Cl₂ / 1 h / 23 °C

6.2: 1.14 g / pyridinium p-toluenesulfonate / CH₂Cl₂; methanol / 5 h / 23 °C

7.1: 88 percent / pyridinium p-toluenesulfonate / acetone / 19 h / 68 °C

8.1: 92 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.5 h / -40 °C

9.1: Dowex 50X₂-100 ion-exchange resin; H₂O / methanol / 12 h / 23 °C

10.1: 0.74 g / Et₃N / methanol / 23 °C

11.1: 89 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 23 °C

12.1: 97 percent / imidazole; DMAP / dimethylformamide / 13 h / 23 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; 18-crown-6 ether; trimethylsilyl cyanide; Dowex 50X₂-100 ion-exchange resin; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; ozone; triethylamine; potassium bromide; lithium diisopropyl amide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/anie.200453697