(2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane

Base Information

• Chemical Name: (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane
• CAS No.: 479673-36-4
• Molecular Formula: C₂₁H₃₆O₄Si
• Molecular Weight: 380.6
• Mol file: 479673-36-4.mol

Synonyms:(2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane

Chemical Property of (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane

There total 6 articles about (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane 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: 64.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (2S,3R,4S)-5-(tert-butyldimethylsilanyloxy)-2,4-dimethylpentane-1,3-diol (480999-22-2) → (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane (479673-36-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; for 3h; Heating;

DOI:10.1021/jm0204136

Reference yield:

(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one (183565-25-5) → (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane (479673-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

2: 64 percent / pyridinium p-toluenesulfonate / benzene / 3 h / Heating

With lithium borohydride; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jm0204136

Reference yield:

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal (104701-87-3) → (2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane (479673-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / Bu₂BOTf; DIPEA

2.1: LiBH₄ / methanol; tetrahydrofuran

2.2: PPTS

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1.1: Evans aldol reaction;

DOI:10.1021/ol026942l

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

(2S,3R,4S)-5-(tert-butyldimethylsilanyloxy)-2,4-dimethylpentane-1,3-diol

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

Downstream raw materials:

(6R, [7R,] [12S,] 13S, [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-7,13, [19-TRIS-(4-METHOXYBENZYLOXY)-6,] 12,14, 20,22-pentamethylhexacosa-2, 4,10, 15,23, 25-hexaenoic acid methyl ester

(4R, [5R,] 10S, [11S,] 12S, [17R,] [18R,] [19R,] 205)-19-(TERT-BUTYLDIMETHYLSILANYLOXY)-5,11, [17-TRIS-(4-METHOXYBENZYLOXY)-4, 10,] 12,18, 20-pentamethyltetracosa-2,8, 13, 21,23-pentaenoic acid ethyl ester

(12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol

(2E,8Z,13Z,21Z)-(4R,5R,10S,11S,12S,17R,18S,19S,20S)-19-(tert-Butyl-dimethyl-silanyloxy)-5,11,17-tris-(4-methoxy-benzyloxy)-4,10,12,18,20-pentamethyl-tetracosa-2,8,13,21,23-pentaen-1-ol