(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 1403608-16-1
• Molecular Formula: C₂₄H₄₀O₅Si
• Molecular Weight: 436.664

Synonyms:(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

There total 5 articles about (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane 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: 88.0%

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (866022-02-8) + p-Methoxybenzyl bromide (2746-25-0) → (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-16-1)

Guidance literature:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 1h;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201200241

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-16-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C

1.2: 1.5 h / 0 °C

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

2.2: -78 - 20 °C

3.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 72 h / -78 - -15 °C / Molecular sieve; Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

4.2: 2 h / 20 °C

With titanium(IV) isopropylate; oxalyl dichloride; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Keck allylation;

DOI:10.1002/ejoc.201200241

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-16-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C

1.2: 1.5 h / 0 °C

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

2.2: -78 - 20 °C

3.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 72 h / -78 - -15 °C / Molecular sieve; Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

4.2: 2 h / 20 °C

With titanium(IV) isopropylate; oxalyl dichloride; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Keck allylation;

DOI:10.1002/ejoc.201200241

upstream raw materials:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

p-Methoxybenzyl bromide

2,3-O-isopropylidene-L-threitol

[(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Downstream raw materials:

{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

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