(4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one

Base Information

• Chemical Name: (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one
• CAS No.: 127725-25-1
• Molecular Formula: C₃₅H₅₄O₉Si
• Molecular Weight: 646.894
• Mol file: 127725-25-1.mol

Synonyms:(4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one

Chemical Property of (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one

There total 8 articles about (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one 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: 90.0%

(2R,4R,6R)-8-(tert-Butyl-diphenyl-silanyloxy)-1-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-4,6-bis-methoxymethoxy-octan-2-ol (127743-56-0) → (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one (127725-25-1)

Guidance literature:

With MeI-CaCO₃; In water; acetonitrile;

DOI:10.1016/S0040-4039(00)99366-3

Reference yield:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3,147220-48-2,116996-54-4) → (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one (127725-25-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / n-BuLi / tetrahydrofuran / -20 °C

2: 81 percent / MeI-CaCO₃ / acetonitrile; H₂O

3: LiAlH(OtBu)3-LiI / diethyl ether / 1 h / -78 °C / 1,3-asymmetric reduction of the β-alkoxy β'-hydroxy ketone with variation of reagent and temperature

4: iPr₂EtN / CH₂Cl₂ / 0 °C

5: pyridinium p-toluenesulfonate (PPTS) / methanol / 45 °C

7: 90 percent / n-BuLi / tetrahydrofuran / -20 °C

8: 90 percent / MeI-CaCO₃ / acetonitrile; H₂O

With n-butyllithium; MeI-CaCO₃; pyridinium p-toluenesulfonate; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)99366-3

Reference yield:

((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane (127725-30-8) → (4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one (127725-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / n-BuLi / tetrahydrofuran / -20 °C

2: 90 percent / MeI-CaCO₃ / acetonitrile; H₂O

With n-butyllithium; MeI-CaCO₃; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/S0040-4039(00)99366-3

upstream raw materials:

(2R,4R,6R)-8-(tert-Butyl-diphenyl-silanyloxy)-1-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-4,6-bis-methoxymethoxy-octan-2-ol

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane

(2S,4R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexane-2,4-diol

Downstream raw materials:

tert-Butyl-[(3R,5S,7R,9S)-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5,7,9-tetrakis-methoxymethoxy-decyloxy]-diphenyl-silane

tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane

(2S,4S,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8-bis-methoxymethoxy-decane-2,4-diol

(2R,4S,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8-bis-methoxymethoxy-decane-2,4-diol