((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol

Base Information

• Chemical Name: ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol
• CAS No.: 1431879-72-9
• Molecular Formula: C₂₀H₃₀O₅Si
• Molecular Weight: 378.541

Synonyms:((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol

Chemical Property of ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol

Chemical Property:

Purity/Quality:

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Technology Process of ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol

There total 5 articles about ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol 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: 65.0%

(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one (1431879-71-8) → ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol (1431879-72-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 2h; Inert atmosphere;

DOI:10.1021/ol400487e

Reference yield:

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol (1431879-69-4) → ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol (1431879-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -60 °C / Inert atmosphere

1.2: 0.33 h / -60 - 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol / 2 h / Inert atmosphere

With n-butyllithium; oxalyl dichloride; sulfur trioxide pyridine complex; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;

DOI:10.1021/ol400487e

Reference yield:

(R)-4-((S)-1-((4-methoxybenzyl)oxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane → ((2R,3S,6R)-6-methoxy-3-((4-methoxybenzyl)oxy)-6-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-2-yl)methanol (1431879-72-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: borane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -60 °C / Inert atmosphere

2.2: 0.33 h / -60 - 0 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 2 h / Inert atmosphere

With n-butyllithium; oxalyl dichloride; borane; sulfur trioxide pyridine complex; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1021/ol400487e

upstream raw materials:

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol

(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

(6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-ol

(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

Downstream 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

(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

(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

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