(2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 762267-53-8
• Molecular Formula: C₂₅H₃₂O₄Si
• Molecular Weight: 424.612
• Mol file: 762267-53-8.mol

Synonyms:(2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol

There total 2 articles about (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-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:

(2R,3S)-6-allyloxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol → (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol (762267-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / DIAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

2: 99 percent / sodium methoxide / methanol / 2 h

3: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

With dmap; di-isopropyl azodicarboxylate; sodium methylate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/ejoc.200400166

Reference yield:

(2R,3R)-6-allyloxy-2-(benzoyloxymethyl)-3,6-dihydro-2H-pyran-3-yl benzoate → (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol (762267-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / sodium methoxide / methanol / 2 h

2: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium methylate; triethylamine; In methanol; dichloromethane;

DOI:10.1002/ejoc.200400166

Reference yield: 85.0%

Trimethyl orthoacetate (1445-45-0) + (2R,3R,6S)-6-allyloxy-2-[(tert-butyldiphenylsilanyloxy)methyl]-3,6-dihydro-2H-pyran-3-ol (762267-53-8) → C28H36O5Si (1403603-20-2)

Guidance literature:

With propionic acid; at 140 ℃; for 72h; Inert atmosphere;

DOI:10.1002/ejoc.201200384

Downstream raw materials:

(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester

(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide