(3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 1290629-85-4
• Molecular Formula: C₂₂H₂₇ClO₅
• Molecular Weight: 406.906
• Mol file: 1290629-85-4.mol

Synonyms:(3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol

There total 9 articles about (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-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:

(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran (1290629-84-3) → (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol (1290629-85-4)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; water; at 20 ℃; for 18h;

Reference yield:

(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran (1290629-84-3) → (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol (1290629-85-4) + (5S,6R,7R,8S)-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol (1290629-70-7)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 18h;

Reference yield:

dapagliflozin (461432-26-8,1373321-04-0) → (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol (1290629-85-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / 18 h / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C

2.2: 18 h / 20 °C

3.1: aluminum (III) chloride / dichloromethane; diethyl ether / 2 h / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -70 °C

4.2: 0.25 h / 20 °C

5.1: sodium hydroxide / 1,4-dioxane; water / 72 h / 20 °C

6.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 8 h / 80 °C

7.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 24 h / 120 °C / sealed tube

8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water; methanol / 18 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; aluminum (III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; hydrogen; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; sodium hydroxide; palladium 10% on activated carbon; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;

upstream raw materials:

(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran

dapagliflozin

(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

(2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran