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

Base Information

• Chemical Name: 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
• CAS No.: 174865-45-3
• Molecular Formula: C₂₇H₄₆O₇Si₂
• Molecular Weight: 538.829
• Mol file: 174865-45-3.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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:

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5) → 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 (174865-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 30 min, 2.) THF, -78 deg C, 5 h 45 min

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

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

4: Py, DMAP / 11 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium dithionite; borane-THF; dihydrogen peroxide; tert.-butyl lithium; In tetrahydrofuran; water;

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-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (174865-45-3)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo951344o

Reference yield:

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) → 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 (174865-45-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Py, DMAP / 11 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; borane-THF; dihydrogen peroxide;

DOI:10.1021/jo951344o

upstream raw materials:

acetic anhydride

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

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

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