(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate

Base Information

• Chemical Name: (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate
• CAS No.: 1431879-84-3
• Molecular Formula: C₅₅H₈₆O₁₀Si₂
• Molecular Weight: 963.453
• Mol file: 1431879-84-3.mol

Synonyms:(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate

Chemical Property of (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate

There total 30 articles about (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate 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: 76.0%

(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate (1431879-97-8) → (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate (1431879-84-3)

Guidance literature:

With (triphenylphosphine)copper(I) hydride hexamer; In water; benzene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol400487e

Reference yield:

tert-Butyl(((E)-5-((2R,6R)-6-methoxy-6-((trimethylsilyl)ethynyl)-5,6-dihydro-2Hpyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane (1431879-77-4) → (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate (1431879-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: chromium dichloride; nickel dichloride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 20 °C

4: (triphenylphosphine)copper(I) hydride hexamer / water; benzene / 12 h / 20 °C / Inert atmosphere

With chromium dichloride; N-iodo-succinimide; (triphenylphosphine)copper(I) hydride hexamer; silver trifluoromethanesulfonate; sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol400487e

Reference yield:

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (1431879-89-8) → (S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate (1431879-84-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 0 °C / Inert atmosphere

2.1: tin(IV) chloride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

2.2: 0.42 h / -78 °C / Inert atmosphere

3.1: dmap; pyridine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

4.1: Pd(OH)2/C; hydrogen / ethyl acetate / 0.25 h / 20 °C

5.1: tin(IV) chloride; triethylsilane / dichloromethane / 1 h / -78 - -30 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 0 °C / Inert atmosphere

7.1: chromium dichloride; nickel dichloride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 20 °C

9.1: (triphenylphosphine)copper(I) hydride hexamer / water; benzene / 12 h / 20 °C / Inert atmosphere

With pyridine; chromium dichloride; triethylsilane; dmap; (triphenylphosphine)copper(I) hydride hexamer; Pd(OH)2/C; hydrogen; sulfur trioxide pyridine complex; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; benzene; 2.1: |Mukaiyama Aldol Addition / 6.1: |Parikh-Doering Oxidation;

DOI:10.1021/ol400487e

upstream raw materials:

tert-Butyl(((E)-5-((2R,6R)-6-methoxy-6-((trimethylsilyl)ethynyl)-5,6-dihydro-2Hpyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane

tert-butyl(((E)-5-((2R,6R)-6-(iodoethynyl)-6-methoxy-5,6-dihydro-2H-pyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentanal

Downstream raw materials:

(2S)-2-[(2R,3R,4aR,5'R,6S,6''R,7aR)-6''[(1E)-5-[(tert-butyldiphenylsilyl)oxy]pent-1-en-1-yl]-3-methyl-3,3''4,4a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-2,2'-oxolane-5',2''-pyran]-6-yl]-2-((triisopropylsilyl)oxy)ethyl pivalate

C₅₃H₈₄O₉Si₂