((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde

Base Information

• Chemical Name: ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde
• CAS No.: 328047-30-9
• Molecular Formula: C₃₁H₄₆O₆Si
• Molecular Weight: 542.788
• Mol file: 328047-30-9.mol

Synonyms:((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde

Chemical Property of ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde

There total 5 articles about ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde 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: 68.0%

(2S,3R,4R,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-ol (328047-26-3) → ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde (328047-30-9)

Guidance literature:

(2S,3R,4R,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-ol; With ozone; In dichloromethane; at -78 - 20 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0040-4039(00)01658-0

Reference yield:

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (196703-95-4) → ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde (328047-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dimethyldioxirane / acetone; CH₂Cl₂ / 90 h / 0 °C

2.1: 80 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: 16 percent / CH₂Cl₂ / 4 h / 20 °C

4.1: 85 percent / L-Selectride / tetrahydrofuran / 1 h / 0 °C

5.1: ozone / CH₂Cl₂ / -78 - 20 °C

5.2: 68 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

With 3,3-dimethyldioxirane; L-Selectride; ozone; In tetrahydrofuran; dichloromethane; acetone; 3.1: Dess Martin oxidation;

DOI:10.1016/S0040-4039(00)01658-0

Reference yield:

((1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-triisopropyl-silane (328047-23-0) → ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde (328047-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.1: 16 percent / CH₂Cl₂ / 4 h / 20 °C

3.1: 85 percent / L-Selectride / tetrahydrofuran / 1 h / 0 °C

4.1: ozone / CH₂Cl₂ / -78 - 20 °C

4.2: 68 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

With L-Selectride; ozone; In tetrahydrofuran; dichloromethane; 2.1: Dess Martin oxidation;

DOI:10.1016/S0040-4039(00)01658-0

upstream raw materials:

(2S,3R,4R,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-ol

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

((1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-triisopropyl-silane

(2S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-triisopropylsilanyloxymethyl-dihydro-pyran-3-one