1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

Base Information

• Chemical Name: 1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol
• CAS No.: 174865-50-0
• Molecular Formula: C₂₅H₄₆O₆Si₂
• Molecular Weight: 498.808
• Mol file: 174865-50-0.mol

Synonyms:

Chemical Property of 1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

There total 1 articles about 1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol 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:

4,4-dimethoxycyclohexa-2,5-dienone (935-50-2) + 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5) → 1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (174865-50-0)

Guidance literature:

With tert.-butyl lithium; Yield given. Multistep reaction; 1.) THF, pentane, -78 deg C, 30 min, 2.) THF, -78 deg C, 5 h 45 min;

DOI:10.1021/jo951344o

Reference yield:

1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (174865-50-0) → 4-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4-hydroxy-cyclohexa-2,5-dienone (174865-51-1)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; water; for 8.5h; Yield given; Ambient temperature;

DOI:10.1021/jo951344o

Reference yield:

1-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (174865-50-0) → Acetic acid (2R,3R,4R,5R)-2-(4-acetoxy-3-bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: Na₂S₂O₄ / tetrahydrofuran; H₂O / 8.5 h / Ambient temperature

2: 1.) BH₃*THF, 2.) 3 N NaOH/H₂O₂ / 1.) 0 deg C -> room temperature, overnight, 2.) MeOH, room temperature, 11 h

3: Py, DMAP / 11 h / Ambient temperature

4: Py, DMAP / 11 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium dithionite; borane-THF; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1021/jo951344o

upstream raw materials:

4,4-dimethoxycyclohexa-2,5-dienone

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose

Downstream raw materials:

4-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4-hydroxy-cyclohexa-2,5-dienone

Acetic acid (2R,3R,4R,5R)-2-(4-acetoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester