2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol

Base Information

• Chemical Name: 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol
• CAS No.: 252904-99-7
• Molecular Formula: C₃₁H₅₈O₇Si₂
• Molecular Weight: 598.968

Synonyms:2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol

Chemical Property of 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol

There total 13 articles about 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol 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:

(2S,3S,4R,5R)-2-(2-Benzyloxy-ethyl)-5-[(S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan → 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol (252904-99-7)

Guidance literature:

With hydrogen; nickel; In ethanol;

DOI:10.1016/j.bmcl.2004.08.069

Reference yield:

(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol (126107-76-4) → 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol (252904-99-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 93 percent / t-BuOK

2.1: n-BuLi / toluene

2.2: 69 percent / BF₃*OEt / toluene / -50 °C

3.1: 99 percent / H₂; quinoline / Pd/CaCO₃ / hexane; CH₂Cl₂ / 20 °C

4.1: 99 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

5.1: aq. OsO₄; NMO / 2-methyl-propan-2-ol / 20 °C

6.1: 58 percent / pyridine / 20 °C

7.1: Triton B / methanol / 20 °C

8.1: methylmagnesium bromide / tetrahydrofuran / 45 °C

9.1: t-BuOK / tetrahydrofuran / 0 °C

10.1: aq. HCl / tetrahydrofuran; methanol / 20 °C

11.1: imidazole / dimethylformamide / 20 °C

12.1: H₂ / Raney Ni / ethanol

With pyridine; 1H-imidazole; quinoline; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; methylmagnesium bromide; potassium tert-butylate; hydrogen; N-benzyl-trimethylammonium hydroxide; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.08.069

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol (252904-99-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 93 percent / t-BuOK

2.1: n-BuLi / toluene

2.2: 69 percent / BF₃*OEt / toluene / -50 °C

3.1: 99 percent / H₂; quinoline / Pd/CaCO₃ / hexane; CH₂Cl₂ / 20 °C

4.1: 99 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

5.1: aq. OsO₄; NMO / 2-methyl-propan-2-ol / 20 °C

6.1: 58 percent / pyridine / 20 °C

7.1: Triton B / methanol / 20 °C

8.1: methylmagnesium bromide / tetrahydrofuran / 45 °C

9.1: t-BuOK / tetrahydrofuran / 0 °C

10.1: aq. HCl / tetrahydrofuran; methanol / 20 °C

11.1: imidazole / dimethylformamide / 20 °C

12.1: H₂ / Raney Ni / ethanol

With pyridine; 1H-imidazole; quinoline; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; methylmagnesium bromide; potassium tert-butylate; hydrogen; N-benzyl-trimethylammonium hydroxide; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.08.069

upstream raw materials:

(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol

p-methoxybenzyl chloride

(2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane

(Z)-(3S,4S)-1-Benzyloxy-7-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxymethyl)-hept-5-en-3-ol

Downstream raw materials:

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

C₅₀H₈₆O₈SSi₂

C₅₂H₉₀O₁₀Si₂

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl) ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate

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