{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

Base Information

Chemical Name:{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester
CAS No.:914983-51-0
Molecular Formula:C₃₃H₄₆O₅Si
Molecular Weight:550.811
Hs Code.:

{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

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Chemical Property of {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

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Technology Process of {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

There total 16 articles about {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl 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:

: {(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1R,2R)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-tetrahydro-pyran-2-yl}-acetic acid allyl ester

: 914983-51-0
{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tetlet.2006.08.055

Reference yield:

: 884338-30-1
(S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

: 914983-51-0
{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: Ph₃P; DEAD / tetrahydrofuran / 0.5 h / 0 - 20 °C

2: K₂CO₃ / methanol / 0.5 h / 20 °C

3: 82 percent / Red-Al / diethyl ether / 3 h / 0 - 20 °C

4: 96 percent / Et₂Zn / CH₂Cl₂ / 4 h / -20 - 0 °C

5: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

6: Zn(BH₄)2 / tetrahydrofuran / 8 h / 0 °C

7: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

8: H₂ / Pd/C / hexane / 1 h / 20 °C

9: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

10: diethyl ether / 1 h / 0 - 20 °C

11: (cHex)2BH / tetrahydrofuran / 1 h / 0 °C

12: H₂O₂; NaOH / H₂O

13: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

14: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

15: K₂CO₃ / dimethylformamide / 0.5 h / 0 - 20 °C

16: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

With dmap; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; diethylzinc; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.08.055

Reference yield:

: 914983-44-1
(R)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

: 914983-51-0
{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 82 percent / Red-Al / diethyl ether / 3 h / 0 - 20 °C

2: 96 percent / Et₂Zn / CH₂Cl₂ / 4 h / -20 - 0 °C

3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

4: Zn(BH₄)2 / tetrahydrofuran / 8 h / 0 °C

5: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

6: H₂ / Pd/C / hexane / 1 h / 20 °C

7: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

8: diethyl ether / 1 h / 0 - 20 °C

9: (cHex)2BH / tetrahydrofuran / 1 h / 0 °C

10: H₂O₂; NaOH / H₂O

11: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

12: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

13: K₂CO₃ / dimethylformamide / 0.5 h / 0 - 20 °C

14: CSA / methanol; CH₂Cl₂ / 0.17 h / 0 °C

With dmap; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; diethylzinc; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2006.08.055