Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester
• CAS No.: 805247-01-2
• Molecular Formula: C₃₄H₅₀O₁₃S₂
• Molecular Weight: 730.895

Synonyms:Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

Chemical Property of Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

There total 7 articles about Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester 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: 58.0%

methanesulfonyl chloride (124-63-0) + Acetic acid (1S,2R)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester → Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester (805247-01-2) + Acetic acid (1S,2S,3S,4R)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.bmcl.2004.08.069

Reference yield:

(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol (126107-76-4) → Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester (805247-01-2)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; quinoline; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; hydrogen; Lindlar's catalyst; In hexane; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.08.069

Reference yield:

p-methoxybenzyl chloride (824-94-2) → Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester (805247-01-2)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; quinoline; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; hydrogen; Lindlar's catalyst; In hexane; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.08.069

upstream raw materials:

methanesulfonyl chloride

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

p-methoxybenzyl chloride

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

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)propyl pivalate

C₅₂H₉₀O₁₀Si₂

C₅₀H₈₆O₈SSi₂

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

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