Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester
• CAS No.: 647842-46-4
• Molecular Formula: C₃₆H₆₆O₈SSi₂
• Molecular Weight: 715.152
• Mol file: 647842-46-4.mol

Synonyms:Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl 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: 86.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3S,4aR,6S,7R,8aS)-2-Hydroxymethyl-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol (647842-45-3) → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (647842-46-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.010

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (647842-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2: H₂ / Pd(OH)2-C / ethyl acetate / 20 °C

3: 86 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogen; palladium hydroxide - carbon; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tetlet.2003.10.010

Reference yield:

(2R,4aR,6S,7R,8aS)-6-(2-Hydroxy-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-3-hydroxy-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (647842-46-4)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide / 0 °C

2: 4-methylmorpholine / CH₂Cl₂ / 20 °C

3: TBAF / tetrahydrofuran / 20 °C

4: 88 percent / SO₃*Py; DMSO; Et₃N / CH₂Cl₂ / 0 °C

5: 92 percent / SmI₂; MeOH / tetrahydrofuran / 0 °C

6: LiAlH₄ / diethyl ether / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

8: H₂ / Pd(OH)2-C / ethyl acetate / 20 °C

9: 86 percent / pyridine / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; samarium diiodide; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5: Nakata cyclization;

DOI:10.1016/j.tetlet.2003.10.010

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3S,4aR,6S,7R,8aS)-2-Hydroxymethyl-7-triisopropylsilanyloxy-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

triisopropylsilyl trifluoromethanesulfonate

((2R,4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester

Downstream raw materials:

{2-[5-[9-benzyloxy-8-(2-benzyloxy-ethyl)-8-methyl-2-vinyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-yloxy]-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-vinyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

[6-benzyloxy-7-(2-benzyloxy-ethyl)-7-methyl-3-triisopropylsilanyloxy-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid 5-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,6-dimethyl-2-vinyl-tetrahydro-pyran-3-yl ester

[6-benzyloxy-7-(2-benzyloxy-ethyl)-3-hydroxy-7-methyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid 5-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,6-dimethyl-2-vinyl-tetrahydro-pyran-3-yl ester

2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol