[(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol

Base Information

• Chemical Name: [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol
• CAS No.: 1290629-79-6
• Molecular Formula: C₄₂H₄₃ClO₆
• Molecular Weight: 679.253

Synonyms:[(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol

Chemical Property of [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol

Chemical Property:

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Safty Information:

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Technology Process of [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol

There total 12 articles about [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol 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: 90.1%

(4aR,6S,7S,8R,8aR)-7,8-dibenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin → [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol (1290629-79-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at 0 - 20 ℃; for 5h;

Reference yield: 84.5%

tert-butyldiphenyl(((2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-2-yl)methoxy)silane → [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol (1290629-79-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.2174/1570180817999200618162949

Reference yield:

(2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran (1290629-78-5) → [(2R,3R,4R,5S,6S)-3,4,5-trisbenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]benzenyl]tetrahydropyran-2-yl]methanol (1290629-79-6)

Guidance literature:

With aluminum (III) chloride; In diethyl ether; dichloromethane; at 0 - 20 ℃;

upstream raw materials:

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

benzaldehyde dimethyl acetal

Downstream raw materials:

{(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate

{(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methyl-tetrahydro-pyran-2-yl}-methanol

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

toluene-4-sulfonic acid (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-ylmethyl ester

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