(2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol
• CAS No.: 114811-23-3
• Molecular Formula: C₂₇H₃₈O₇
• Molecular Weight: 474.595
• Mol file: 114811-23-3.mol

Synonyms:(2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

Chemical Property of (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

There total 24 articles about (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol 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: 84.0%

Benzoic acid (2R,3S,4S)-3-hydroxy-4-[(4R,5R)-5-[(S)-1-(4-methoxy-benzyloxy)-propyl]-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-2-methyl-pentyl ester (114825-81-9) → (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol (114811-23-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)96566-3

Reference yield: 76.0%

(2R,3S,4S,5R,6R,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylenedioxy>-2,4,6-trimethylnonan-3-ol (114825-81-9) → (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol (114811-23-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 13h; Ambient temperature;

DOI:10.1248/cpb.37.1160

Reference yield:

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane (87641-44-9,98049-27-5) → (2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol (114811-23-3)

Guidance literature:

Multi-step reaction with 13 steps

1: pyridine / CH₂Cl₂ / 0 deg C, rt, 10.5 h

2: CSA / CH₂Cl₂ / 2 h / Ambient temperature

3: 1N KOH / methanol / 18 h / Ambient temperature

4: 94 percent / oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -60 - -50 °C

5: 99 percent / LDA / tetrahydrofuran / -83 deg C, -20 deg C, 2 h

6: 90 percent / Et₃N / benzene / 0.33 h / 7 °C

7: 99 percent / NaOEt / tetrahydrofuran / 3.5 h / Ambient temperature

8: 78 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

9: m-CPBA / CH₂Cl₂ / 2.5 h / -20 °C

10: 1M n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

11: 46 percent / H₂ / 5percent Pt-C / benzene / 1 h / 8 - 10 °C

12: 84 percent / pyridine / CH₂Cl₂ / 35 h / Ambient temperature

13: 76 percent / 4N HCl / tetrahydrofuran / 13 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1248/cpb.37.1160

upstream raw materials:

Benzoic acid (2R,3S,4S)-3-hydroxy-4-[(4R,5R)-5-[(S)-1-(4-methoxy-benzyloxy)-propyl]-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-2-methyl-pentyl ester

(2R,3S,4S,5R,6R,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylenedioxy>-2,4,6-trimethylnonan-3-ol

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

benzoyl chloride

Downstream raw materials:

(2R,3S,4S,5R,6R,7R)-1-benzyloxy-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-6-ol

(2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol

(2R,3S,4S,5R,6R,7R)-1-benzoyloxy-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonane

(2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal