(αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol

Base Information

• Chemical Name: (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol
• CAS No.: 197246-55-2
• Molecular Formula: C₂₄H₃₈O₅Si
• Molecular Weight: 434.648

Synonyms:(αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol

Chemical Property of (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol

There total 15 articles about (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol 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:

(3R,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]-oxy]-3-methyl-5-phenylmethoxy-1-pentene (197246-49-4) → (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol (197246-55-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 23 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O; benzene / 16 h / 20 °C

2.1: pyridine; DMAP / 1 h / 0 °C

3.1: pyridine; DMAP / 12 h / 20 °C

4.1: 0.321 g / sodium methoxide / methanol / 0.5 h / 0 °C

5.1: n-butyl lithium / tetrahydrofuran; hexane / 0.33 h / -78 - -30 °C

5.2: borontrifluoride etherate / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.1: 0.501 g / pyridinium p-toluenesulfonate / tetrahydrofuran; H₂O / 3 h

With pyridine; dmap; n-butyllithium; sodium methylate; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; water; acetone; benzene; 1.1: dihydroxylation / 2.1: Esterification / 3.1: Esterification / 4.1: Cyclization / 5.1: Metallation / 5.2: Addition / 6.1: Hydrolysis;

DOI:10.1016/S0040-4020(97)00865-X

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol (197246-55-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 29.9 g / imidazole; DMAP / dimethylformamide / 12 h

2.1: 23 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O; benzene / 16 h / 20 °C

3.1: pyridine; DMAP / 1 h / 0 °C

4.1: pyridine; DMAP / 12 h / 20 °C

5.1: 0.321 g / sodium methoxide / methanol / 0.5 h / 0 °C

6.1: n-butyl lithium / tetrahydrofuran; hexane / 0.33 h / -78 - -30 °C

6.2: borontrifluoride etherate / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: 0.501 g / pyridinium p-toluenesulfonate / tetrahydrofuran; H₂O / 3 h

With pyridine; 1H-imidazole; dmap; n-butyllithium; sodium methylate; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone; benzene; 1.1: silylation / 2.1: dihydroxylation / 3.1: Esterification / 4.1: Esterification / 5.1: Cyclization / 6.1: Metallation / 6.2: Addition / 7.1: Hydrolysis;

DOI:10.1016/S0040-4020(97)00865-X

Reference yield:

(2S,3R,4S)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-[5-(1-methoxy-1-methyl-ethoxymethyl)-furan-2-yl]-3-methyl-pentan-2-ol → (αS,1'R,2'S)-α-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-5-hydroxymethyl-2-furaneethanol (197246-55-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In tetrahydrofuran; water; for 3h;

DOI:10.1016/S0040-4020(97)00865-X

upstream raw materials:

2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle

methyl 2,3-anhydro-5-O-benzyl-α-D-ribofuranoside

tert-butyldimethylsilyl chloride

(3R,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]-oxy]-3-methyl-5-phenylmethoxy-1-pentene

Downstream raw materials:

(4S,6R,1'R,2'S)-2,2-dimethyl-4-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxa-spiroundec-10-en-9-one

[4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one

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