(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

Base Information

Chemical Name:(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol
CAS No.:489440-30-4
Molecular Formula:C₄₀H₇₄O₉SSi₂
Molecular Weight:787.259
Hs Code.:

Synonyms:(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

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Chemical Property of (2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

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Technology Process of (2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

There total 7 articles about (2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol 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: 42.0%

: 489440-25-7
(2R)-2-{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}propanal

: 489440-28-0
(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

: 489440-30-4
(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

Guidance literature:: (4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

(2R)-2-{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}propanal; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y

Reference yield:

: 110454-08-5
(4S,5S)-2,2-dimethyl-4,5-bis(1-methylvinyl)-1,3-dioxolane

: 489440-30-4
(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: borane*DMSO; triethylborane / dimethylsulfoxide; hexane; diethyl ether / 12 h

1.2: 50 percent / H₂O₂; NaOH; water / 4 h / 20 °C

2.1: 73 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

3.1: 99 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

4.1: 87 percent / sodium iodide / dimethylformamide / 12 h / 70 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: 42 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; triethyl borane; borane*DMSO; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y

Reference yield:

: 81706-69-6
(4R,trans)-2,2,α,α,α',α'-hexamethyl-1,3-dioxolane-4,5-dimethanol

: 489440-30-4
(2R,3RS,4RS,5R)-2,5-bis{(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-1,3-dioxolane-4-yl}-4-phenylsulfonylhexan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / methanesulfonyl chloride; 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 30 h / 20 °C

2.1: borane*DMSO; triethylborane / dimethylsulfoxide; hexane; diethyl ether / 12 h

2.2: 50 percent / H₂O₂; NaOH; water / 4 h / 20 °C

3.1: 73 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

4.1: 99 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

5.1: 87 percent / sodium iodide / dimethylformamide / 12 h / 70 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.2: 42 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; triethyl borane; borane*DMSO; sodium hydride; methanesulfonyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y