(+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol

Base Information

• Chemical Name: (+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol
• CAS No.: 291751-49-0
• Molecular Formula: C₂₅H₄₄O₆Si
• Molecular Weight: 468.706
• Mol file: 291751-49-0.mol

Synonyms:(+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol

Chemical Property of (+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol

There total 1 articles about (+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol 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: 94.0%

(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene (291751-48-9) → (+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol (291751-49-0)

Guidance literature:

(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene; With ozone; In methanol; dichloromethane; at -95 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at 0 ℃; for 3h; Further stages.;

DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

Reference yield: 82.0%

(+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol (291751-49-0) → (+)-(2R,3S,4S,5R,6S)-[10-p-(methoxyphenyl)-5-methyl-4-(triisopropylsilyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl]methanol

Guidance literature:

With 3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at -60 - 0 ℃; for 4h;

DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

Reference yield:

(+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol (291751-49-0) → (+)-(2R,3S,4S,5R,6S)-[10-p-(methoxyphenyl)-5-methyl-4-(triisopropylsilyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl]carbaldehyde

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / DDQ; molecular sieves 3 Angstroem / CH₂Cl₂ / 4 h / -60 - 0 °C

2: 79 percent / NMO; molecular sieves 3 Angstroem; Pr₄NRuO₄ / CH₂Cl₂ / 1 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; 1: oxidative ring closure / 2: Oxidation;

DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

upstream raw materials:

(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene