{(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Base Information

• Chemical Name: {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester
• CAS No.: 879873-94-6
• Molecular Formula: C₂₉H₄₈O₆Si
• Molecular Weight: 520.782
• Mol file: 879873-94-6.mol

Synonyms:{(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Chemical Property of {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester

There total 16 articles about {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester 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: 69.0%

{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester (879873-93-5) + t-butyldimethylsiyl triflate (69739-34-0) → {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester (879873-94-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.5012/bkcs.2010.31.03.653

Reference yield:

5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester (879873-92-4) + t-butyldimethylsiyl triflate (69739-34-0) → {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester (879873-94-6)

Guidance literature:

5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h;

t-butyldimethylsiyl triflate; With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol052851n

Reference yield:

4-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)butan-2-one (879873-85-5) → {(2S,3S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester (879873-94-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: iPr₂NEt; Bu₂BOTf / diethyl ether / 2 h / -78 °C

1.2: 93 percent / H₂O₂ / ethanol; methanol / 1 h / 20 °C / pH 7

2.1: 95 percent / Me₄NB(OAc)3H; AcOH / acetonitrile / 48 h / -20 °C

3.1: 83 percent / PPTS / CH₂Cl₂ / 5 h / 20 °C

4.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: 89 percent / iPr₂NEt; LiCl / acetonitrile / 5 h / 0 - 20 °C

7.1: 97 percent / 10-camphorsulfonic acid; H₂O / methanol / 2.5 h / 20 °C

8.1: NaH / tetrahydrofuran / 4 h / 20 °C

8.2: 335.8 mg / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 1.1: aldol reaction / 5.1: Dess-Martin oxidation / 6.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ol052851n

upstream raw materials:

5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

t-butyldimethylsiyl triflate

4-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)butan-2-one

1-Methoxy-4-[(S)-3-methyl-1-((1R,2R)-2-methyl-cyclopropyl)-but-3-enyloxymethyl]-benzene