(2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde

Base Information

• Chemical Name: (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde
• CAS No.: 1289513-06-9
• Molecular Formula: C₂₈H₅₀O₆Si₂
• Molecular Weight: 538.872
• Mol file: 1289513-06-9.mol

Synonyms:(2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde

Chemical Property of (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde

There total 4 articles about (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde 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: 93.0%

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carboxylate (1289513-05-8) → (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde (1289513-06-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -90 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/ejoc.201001411

Reference yield:

(2S,3R,5R)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-5-methyl-tetrahydro-furan-2-carboxylic acid methyl ester (1063693-99-1) → (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde (1289513-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 0.92 h / -78 °C / Inert atmosphere

2: trityl tetrafluoroborate / dichloromethane / 0 - 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -90 °C / Inert atmosphere

With 2,6-dimethylpyridine; trityl tetrafluoroborate; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1002/ejoc.201001411

Reference yield:

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-hydroxyethyl}-5-methyltetrahydrofuran-2-carboxylate (1289513-04-7) → (2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde (1289513-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: trityl tetrafluoroborate / dichloromethane / 0 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -90 °C / Inert atmosphere

With trityl tetrafluoroborate; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1002/ejoc.201001411

upstream raw materials:

(2S,3R,5R)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-5-methyl-tetrahydro-furan-2-carboxylic acid methyl ester

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-hydroxyethyl}-5-methyltetrahydrofuran-2-carboxylate

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carboxylate

t-butyldimethylsiyl triflate

Downstream raw materials:

(R)-6-[(benzyloxy)methyl]-1-((2R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

(1R,3S)-6-[(benzyloxy)methyl]-1-((2R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-yl)-3-methylhept-6-ene-1,3-diol

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy](tert-butyl)dimethylsilane

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol