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

Base Information

• Chemical Name: (S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol
• CAS No.: 884338-30-1
• Molecular Formula: C₃₅H₄₄O₄Si
• Molecular Weight: 556.817
• Mol file: 884338-30-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-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:

[(2S,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-acetaldehyde + prop-1-yne (74-99-7) → (S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol (884338-30-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

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

Guidance literature:

Multi-step reaction with 14 steps

1.1: CH₂Cl₂ / 4 h / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

3.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

3.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

4.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6.1: CSA / methanol / 48 h / 20 °C

7.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

8.1: TBAF / tetrahydrofuran / 3 h / 0 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

10.1: DIBAL-H

11.1: (+)-DIPT

12.1: CCl₄; Ph₃P; NaHCO₃

13.1: LDA

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; oxalyl dichloride; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless epoxidation / 9.1: Swern oxidation / 12.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol (884338-24-3) → (S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol (884338-30-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

1.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

2.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

4.1: CSA / methanol / 48 h / 20 °C

5.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 3 h / 0 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: DIBAL-H

9.1: (+)-DIPT

10.1: CCl₄; Ph₃P; NaHCO₃

11.1: LDA

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; dmap; oxalyl dichloride; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless epoxidation / 7.1: Swern oxidation / 10.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

prop-1-yne

methyl iodide

(2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol

Downstream raw materials:

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

(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-2-vinyl-tetrahydro-pyran

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

(2R,3S,4S,6R)-2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-tetrahydro-pyran