2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol

Base Information

• Chemical Name: 2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol
• CAS No.: 884338-29-8
• Molecular Formula: C₃₂H₄₂O₄Si
• Molecular Weight: 518.769

Synonyms:2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about 2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol 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:

2-benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran → 2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol (884338-29-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 3h;

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 → 2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol (884338-29-8)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

2-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethanol → 2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol (884338-29-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: CH₂Cl₂ / 4 h / 20 °C

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

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

4.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

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

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

7.1: CSA / methanol / 48 h / 20 °C

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

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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 4.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

(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

(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

Downstream raw materials:

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

(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

(1S,5S,7R,9S,10S,11S,15S,17R,19S,20S)-9,19-Bis-(tert-butyl-diphenyl-silanyloxy)-10,20-dimethyl-5,15-bis-((1S,2S)-2-methyl-cyclopropyl)-4,14,21,22-tetraoxa-tricyclo[15.3.1.1^7,11]docosane-3,13-dione

{4-(tert-butyl-diphenyl-silanyloxy)-6-[2-({4-(tert-butyl-diphenyl-silanyloxy)-6-[2-hydroxy-2-(2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetoxy)-2-(2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid

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