(3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane

Base Information

• Chemical Name: (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane
• CAS No.: 692753-40-5
• Molecular Formula: C₂₅H₄₄N₄O₅SSi
• Molecular Weight: 540.8
• Mol file: 692753-40-5.mol

Synonyms:(3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane

Chemical Property of (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane

There total 10 articles about (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane 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: 91.0%

t-butyldimethylsiyl triflate (69739-34-0) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) + (3S,4S)-4-(methoxymethoxy)decane-1,3-diol (692753-39-2) → (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane (692753-40-5)

Guidance literature:

1-Phenyl-1H-tetrazole-5-thiol; (3S,4S)-4-(methoxymethoxy)decane-1,3-diol; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

With dihydrogen peroxide; ammonium heptamolybdate; In ethanol;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane;

DOI:10.3987/COM-04-10016

Reference yield:

(E)-1-(4-methoxybenzyloxy)-3-decene (862907-35-5) → (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane (692753-40-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 11.5 g / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 4 °C

2: DDQ / CH₂Cl₂ / 1 h / 20 °C

3: i-Pr₂NEt / CH₂Cl₂ / 20 °C

4: 3.6 g / AcOH; H₂O / tetrahydrofuran / 2 h / Heating

5: PPh₃; DIAD / tetrahydrofuran; toluene / 0.33 h / 0 °C

6: (NH₄)6Mo₇O₂₄*4H₂O; aq. H₂O₂ / ethanol / 6 h / 20 °C

7: 4.2 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; ammonium heptamolybdate; AD-mix-α; methanesulfonamide; di-isopropyl azodicarboxylate; water; dihydrogen peroxide; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 5: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.05.057

Reference yield:

(1S)-1-[(4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]heptan-1-ol (862907-36-6) → (3S,4S)-3-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decane (692753-40-5)

Guidance literature:

Multi-step reaction with 5 steps

1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

2: 3.6 g / AcOH; H₂O / tetrahydrofuran / 2 h / Heating

3: PPh₃; DIAD / tetrahydrofuran; toluene / 0.33 h / 0 °C

4: (NH₄)6Mo₇O₂₄*4H₂O; aq. H₂O₂ / ethanol / 6 h / 20 °C

5: 4.2 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; ammonium heptamolybdate; di-isopropyl azodicarboxylate; water; dihydrogen peroxide; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; toluene; 3: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.05.057

upstream raw materials:

t-butyldimethylsiyl triflate

1-Phenyl-1H-tetrazole-5-thiol

(3S,4S)-4-(methoxymethoxy)decane-1,3-diol

(3S,4S)-4-(methoxymethoxy)-1-(1-phenyl-1H-tetrazole-5-sulfonyl)decan-3-ol