(S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one

Base Information

• Chemical Name: (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one
• CAS No.: 1450741-63-5
• Molecular Formula: C₄₃H₅₀O₁₁
• Molecular Weight: 742.863

Synonyms:(S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one

Chemical Property of (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one

There total 16 articles about (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one 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:

C46H58O11Si (1450741-65-7) → (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one (1450741-63-5)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 0.25h; diastereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol402191t

Reference yield:

(benzyloxy)methyl 3,5-bis((benzyloxy)methoxy)-4-bromobenzoate (1450741-52-2) → (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one (1450741-63-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0.25 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

2.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique

3.1: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

4.1: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / Inert atmosphere; Schlenk technique

5.1: tetrahydrofuran; diethyl ether / 0.25 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

6.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium osmate; potassium carbonate; methanesulfonamide / water; tert-butyl alcohol / 18 h / 20 °C / Inert atmosphere; Schlenk technique

7.1: iodine; silver trifluoroacetate / chloroform / 1.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

8.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr / Schlenk technique

9.1: triethylamine; dmap / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique

10.1: boron trifluoride diethyl etherate / dichloromethane / 0.05 h / -78 °C / Inert atmosphere; Schlenk technique

10.2: 1.5 h / -78 °C / Inert atmosphere; Schlenk technique

11.1: potassium carbonate / methanol; water / 0.25 h / 20 °C / Inert atmosphere; Schlenk technique

With dmap; potassium osmate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; methanesulfonamide; boron trifluoride diethyl etherate; potassium tert-butylate; iodine; palladium diacetate; silver trifluoroacetate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); ruphos; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: |Wittig Olefination / 4.1: |Suzuki Coupling / 6.1: |Sharpless Dihydroxylation / 10.1: |Mukaiyama Aldol Addition / 10.2: |Mukaiyama Aldol Addition;

DOI:10.1021/ol402191t

Reference yield:

3,5-bis((benzyloxy)methoxy)-4-bromobenzaldehyde (1450741-54-4) → (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one (1450741-63-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2.1: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / Inert atmosphere; Schlenk technique

3.1: tetrahydrofuran; diethyl ether / 0.25 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

4.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium osmate; potassium carbonate; methanesulfonamide / water; tert-butyl alcohol / 18 h / 20 °C / Inert atmosphere; Schlenk technique

5.1: iodine; silver trifluoroacetate / chloroform / 1.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

6.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr / Schlenk technique

7.1: triethylamine; dmap / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique

8.1: boron trifluoride diethyl etherate / dichloromethane / 0.05 h / -78 °C / Inert atmosphere; Schlenk technique

8.2: 1.5 h / -78 °C / Inert atmosphere; Schlenk technique

9.1: potassium carbonate / methanol; water / 0.25 h / 20 °C / Inert atmosphere; Schlenk technique

With dmap; potassium osmate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; methanesulfonamide; boron trifluoride diethyl etherate; potassium tert-butylate; iodine; palladium diacetate; silver trifluoroacetate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); ruphos; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: |Wittig Olefination / 2.1: |Suzuki Coupling / 4.1: |Sharpless Dihydroxylation / 8.1: |Mukaiyama Aldol Addition / 8.2: |Mukaiyama Aldol Addition;

DOI:10.1021/ol402191t

upstream raw materials:

(benzyloxy)methyl 3,5-bis((benzyloxy)methoxy)-4-bromobenzoate

(3,5-bis((benzyloxy)methoxy)-4-bromophenyl)methanol

3,5-bis((benzyloxy)methoxy)-4-bromobenzaldehyde

3,5-bis((benzyloxy)methoxy)-4-bromo-1-(E)-prop-1-en-1-ylbenzene

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