(2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1204220-79-0
• Molecular Formula: C₂₃H₂₇ClO₆
• Molecular Weight: 434.917

Synonyms:(2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 4 articles about (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-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: 60.0%

methanol (67-56-1) + 4-bromo-1-chloro-2-(4-cyclopropylbenzyl)benzene (1204220-77-8) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1204220-79-0)

Guidance literature:

4-bromo-1-chloro-2-(4-cyclopropylbenzyl)benzene; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; at 40 ℃; for 2.5h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; n-heptane; at 20 ℃; for 3h;

methanol; With hydrogenchloride; at 20 ℃; for 16h;

Reference yield: 55.0%

methanol (67-56-1) + 1-chloro-2-(4-cyclopropylbenzyl)-4-iodobenzene (1459754-53-0) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1204220-79-0)

Guidance literature:

1-chloro-2-(4-cyclopropylbenzyl)-4-iodobenzene; With TurboGrignard; In tetrahydrofuran; at 0 ℃; for 2.16667h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; n-heptane; at -5 - 0 ℃; for 3h;

methanol; With hydrogenchloride; In tetrahydrofuran; n-heptane; at 0 - 20 ℃; for 16h;

Reference yield: 0.6%

methanol (67-56-1) + 4-bromo-1-chloro-2-(4-cyclopropylbenzyl)benzene (1204220-77-8) + D-Glucono-1,5-lactone (90-80-2,1335-57-5,4253-68-3) → (2S,3R,4R,5S,6R)-2-methoxy-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1204220-79-0)

Guidance literature:

4-bromo-1-chloro-2-(4-cyclopropylbenzyl)benzene; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; at 40 ℃; for 2.5h; Inert atmosphere;

D-Glucono-1,5-lactone; In tetrahydrofuran; n-heptane; at 20 ℃; for 3h;

methanol; In tetrahydrofuran; n-heptane; water; at 20 ℃; for 16h; Reagent/catalyst; Temperature; Concentration;

upstream raw materials:

methanol

4-bromo-1-chloro-2-(4-cyclopropylbenzyl)benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

1-chloro-2-(4-cyclopropylbenzyl)-4-iodobenzene

Downstream raw materials:

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-cyclopropylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

5-chloro-4-(4-ethylbenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzoic acid

(5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methan-d2-ol

methyl 5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzoate

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