(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

Base Information

Chemical Name:(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran
CAS No.:128329-80-6
Molecular Formula:C₃₁H₅₈O₄Si₂
Molecular Weight:550.97
Hs Code.:

Synonyms:(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

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Chemical Property of (1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

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Technology Process of (1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

There total 6 articles about (1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran 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: 94.0%

: 133732-91-9
tert-butyldimethylsilyl triflate

: 128329-79-3
(1''R,1'R,2R,5S)-5-(1'-hydroxyethyl)-5-methyl-2-(1''-hydroxy-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

: 128329-80-6
(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ja00169a042

Reference yield:

: 128329-76-0
(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-4-methylene-3,9-dioxabicyclo<4.2.1>nonane

: 128329-80-6
(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / pyridinium tosylate / CH₂Cl₂ / 6 h / 20 °C

2: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h

3: 55 percent / CH₂Cl₂; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h

4: 94 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

With dimethylsulfide; pyridinium p-toluenesulfonate; ozone; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja00169a042

Reference yield:

: 128329-77-1
(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

: 128329-80-6
(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h

2: 55 percent / CH₂Cl₂; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h

3: 94 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

With dimethylsulfide; ozone; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja00169a042