2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid

Base Information

• Chemical Name: 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid
• CAS No.: 1381848-85-6
• Molecular Formula: C₄₆H₇₄O₉Si₂
• Molecular Weight: 827.259

Synonyms:2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid

Chemical Property of 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid

There total 36 articles about 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid 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: 97.0%

(2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-(((2S,4S,5S,6S)-6-(2-hydroxyethyl)-5-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)-2-methoxy-4-methyldihydro-2H-pyran-3(4H)-one (1381848-83-4) → 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid (1381848-85-6)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 6.5h;

DOI:10.1021/ol301278e

Reference yield:

(4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-2-methyl-3-((triethylsilyl)oxy)butan-2-yl)-4-methyltetrahydro-2H-pyran-2-one (1381848-71-0) → 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid (1381848-85-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C

2.2: 0.67 h

2.3: 14 h / 20 °C

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / methanol; dichloromethane / 1.5 h / 0 °C

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 27 h / 0 - 20 °C / Molecular sieve

5.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.5 h / 20 °C

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6.5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1021/ol301278e

Reference yield:

(2R,4R)-2-((S)-4-((tert-butyldiphenylsilyl)oxy)-2-methyl-3-((triethylsilyl)oxy)butan-2-yl)-4-methyl-3,4-dihydro-2H-pyran-6-yl trifluoromethanesulfonate (1381848-73-2) → 2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid (1381848-85-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: 0.67 h

1.3: 14 h / 20 °C

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / methanol; dichloromethane / 1.5 h / 0 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 27 h / 0 - 20 °C / Molecular sieve

4.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.5 h / 20 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6.5 h / 20 °C

With tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol301278e

upstream raw materials:

triisopropyl(((2S,3S,4S)-2-(2-((4-methoxybenzyl)oxy)ethyl)-3-methyl-6-methylenetetrahydro-2H-pyran-4-yl)oxy)silane

C₁₇H₃₆O₂Si

C₁₇H₃₈O₄Si

C₃₃H₅₆O₄Si₂

Downstream raw materials:

(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

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