(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Base Information

Chemical Name:(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one
CAS No.:1415310-39-2
Molecular Formula:C₄₈H₇₀O₆Si₂
Molecular Weight:799.251
Hs Code.:

(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Synonyms:(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

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Chemical Property of (4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

There total 17 articles about (4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-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: 70.0%

: 1415310-30-3
(4S,6S)-6-(but-3-enyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxane-4-carboxamide

: 1415310-36-9
C₃₇H₅₃BrO₃Si₂

: 1415310-39-2
(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Guidance literature:: C₃₇H₅₃BrO₃Si₂; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.666667h;

(4S,6S)-6-(but-3-enyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxane-4-carboxamide; In diethyl ether; pentane; at 0 ℃; for 3h;
DOI:10.1039/c2ob26641e

Reference yield:

: 1415310-78-9
1-(2-but-3-enyl-1,3-dioxolan-2-yl)-3-((R)-p-tolylsulfinyl)propan-2-one

: 1415310-39-2
(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

2.1: 10-camphorsufonic acid / acetone / 24 h / 20 °C

3.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.33 h / -78 °C

3.2: 4 h / -78 °C

4.1: pyridinium p-toluenesulfonate / acetone / 16 h / 20 °C

5.1: trifluoroacetic anhydride; 2,4,6-trimethyl-pyridine / acetonitrile / 0.75 h / 0 °C

5.2: 1.5 h / 20 °C

6.1: 2-methyl-but-2-ene; sodium chlorite; potassium dihydrogenphosphate / water; tert-butyl alcohol / 5.5 h

7.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C

7.2: 20 °C

8.1: tert.-butyl lithium / diethyl ether; pentane / 0.67 h / -78 °C

8.2: 3 h / 0 °C

With 2,4,6-trimethyl-pyridine; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl methoxy borane; 10-camphorsufonic acid; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 1,1'-carbonyldiimidazole; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; pentane; 5.1: |Pummerer Sulfoxide Rearrangement;
DOI:10.1039/c2ob26641e

Reference yield:

: 1415310-84-7
C₁₈H₂₆O₃S

: 1415310-39-2
(4S,5S)-5-(benzyloxy)-1-((4S,6S)-6-(but-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)-8-((tert-butyldiphenylsilyl)oxy)-2-methyleneoctan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: trifluoroacetic anhydride; 2,4,6-trimethyl-pyridine / acetonitrile / 0.75 h / 0 °C

1.2: 1.5 h / 20 °C

2.1: 2-methyl-but-2-ene; sodium chlorite; potassium dihydrogenphosphate / water; tert-butyl alcohol / 5.5 h

3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C

3.2: 20 °C

4.1: tert.-butyl lithium / diethyl ether; pentane / 0.67 h / -78 °C

4.2: 3 h / 0 °C

With 2,4,6-trimethyl-pyridine; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; tert.-butyl lithium; 1,1'-carbonyldiimidazole; trifluoroacetic anhydride; In diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol; pentane; 1.1: |Pummerer Sulfoxide Rearrangement;
DOI:10.1039/c2ob26641e