((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Base Information

• Chemical Name: ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester
• CAS No.: 321667-23-6
• Molecular Formula: C₃₆H₅₂O₇Si
• Molecular Weight: 624.89

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

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

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

There total 2 articles about ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-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: 93.0%

[(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-methoxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (321667-21-4) → ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester (321667-23-6)

Guidance literature:

[(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-methoxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 16h; Further stages.;

DOI:10.1021/ja003593m

Reference yield:

[(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-hydroxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (321667-19-0) → ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester (321667-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / 4 Angstroem molecular sieves; Proton Sponge (R) / CH₂Cl₂ / 0.83 h

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 93 percent / PPh₃ / CH₂Cl₂ / 16 h / 20 °C

With Proton Sponge; 4 A molecular sieve; ozone; In dichloromethane;

DOI:10.1021/ja003593m

Reference yield:

4-methylpentyne (7154-75-8) + ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester (321667-23-6) → ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-3-[(2R,3S,6S)-6-((E)-(S)-2-hydroxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methoxy-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester + ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-3-[(2R,3S,6S)-6-((E)-(R)-2-hydroxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methoxy-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester (321667-25-8)

Guidance literature:

4-methylpentyne; With dimethylsulfide borane complex; cyclohexene; In hexane; at 20 ℃; for 1h;

With titanium(IV) isopropylate; N,N-dibutylaminoethanol; diethylzinc; In hexane; toluene; at 50 ℃; for 0.5h;

((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester; In hexane; toluene; at -20 ℃; for 20h; Further stages.;

DOI:10.1021/ja003593m

upstream raw materials:

[(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-methoxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

[(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-hydroxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Downstream raw materials:

((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-3-[(2R,3S,6S)-6-((E)-(R)-2-hydroxy-6-methyl-hept-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methoxy-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

(1R,3S,5R,7R,9R,13R,15S,18S)-7-(tert-butyldiphenylsilanyloxy)-3-methoxy-18-methyl-13-((E)-4-methylpent-1-enyl)-12,19,20-trioxatricyclo[13.3.1.1^5,9]icosan-11-one

[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

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