(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

Base Information

Chemical Name:(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol
CAS No.:114811-25-5
Molecular Formula:C₅₈H₈₄O₁₁SSi
Molecular Weight:1017.45
Hs Code.:

(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

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Chemical Property of (2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

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Technology Process of (2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

There total 30 articles about (2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol 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: 86.0%

: 114825-89-7
(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal

: 114825-85-3,114884-10-5
(2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxyylsulfinyl-2,4,6-trimethylnonane

: 114811-25-5,124987-18-4,124987-19-5,124987-20-8,124987-21-9
(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; -15 deg C, 30 min, -80 deg C, 1 h;
DOI:10.1248/cpb.37.1167

Reference yield:

: 114811-23-3
(2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

: 114811-25-5,124987-18-4,124987-19-5,124987-20-8,124987-21-9
(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / PPTS / CH₂Cl₂ / Ambient temperature

2: iPr₂EtN / CH₂Cl₂ / 45 °C

3: NaOH / dioxane / 65 - 75 °C

4: Et₃N, DMAP / CH₂Cl₂ / Heating

5: 2.) NaIO₄ / 1.) EtOH, DME, reflux, 2.) MeOH, H₂O, room temp.

6: 85 percent / LDA / tetrahydrofuran / 1.5 h / -80 - -70 °C

With dmap; sodium hydroxide; sodium periodate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; pyridinium p-toluenesulfonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/S0040-4039(00)96566-3

Reference yield:

: Benzoic acid (2R,3R,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

: 114811-25-5,124987-18-4,124987-19-5,124987-20-8,124987-21-9
(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

Guidance literature:: Multi-step reaction with 9 steps

1: CSA / CH₂Cl₂ / Ambient temperature

2: 96 percent / H₂ / Pd-C / ethanol

3: 82 percent / PCC / CH₂Cl₂ / Ambient temperature; molecular sieves

4: 86 percent / n-BuLi / tetrahydrofuran / -75 - -70 °C

5: 92 percent / TsOH*H₂O / methanol / Ambient temperature

6: 93 percent / imidazole / dimethylformamide / Ambient temperature

7: 95 percent / PPTS / Ambient temperature

8: 88 percent / MeI, NaHCO₃ / acetonitrile; H₂O / 70 °C

9: 85 percent / LDA / tetrahydrofuran / 1.5 h / -80 - -70 °C

With 1H-imidazole; n-butyllithium; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)96566-3