(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

Base Information

Chemical Name:(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene
CAS No.:947373-37-7
Molecular Formula:C₃₂H₅₄N₂O₆S₂Si₂
Molecular Weight:683.094
Hs Code.:

Synonyms:(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

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Chemical Property of (2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

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Technology Process of (2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

There total 1 articles about (2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene 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: 72.0%

: 947373-35-5
(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

: 18522-92-4
sodium p-toluenesulfonamide

: 947373-37-7
(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

Guidance literature:: In dimethyl sulfoxide; at 80 ℃; for 12h;
DOI:10.1021/jo070462w

Reference yield: 81.0%

: 947373-37-7
(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

: 947373-38-8
(2R)-N-[2-(tert-butyldimethylsilyloxy)-3-oxopropyl]-4-methylbenzenesulfonamide

Guidance literature:: (2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene; With ozone; In dichloromethane; at -78 ℃; for 0.166667h; under 155.149 Torr;

With thiourea; In dichloromethane; at 0 ℃; for 3h; Further stages.;
DOI:10.1021/jo070462w

Reference yield:

: 947373-37-7
(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

: 947373-47-9
methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C / 155.15 Torr

1.2: 81 percent / thiourea / CH₂Cl₂ / 3 h / 0 °C

2.1: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 14 h / -78 °C

3.1: 78 percent / (i-Pr₂)NEt / CHCl₃ / 6 h / Heating

4.1: 88 percent / NaBH₄ / ethanol / 7 h / 20 °C

5.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.25 h / -60 - 0 °C

6.1: 315 mg / CH₂Cl₂ / 5 h / 0 - 20 °C

7.1: 93 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; chloroform; ethyl acetate; 5.1: Swern oxidation / 6.1: Wittig reaction;
DOI:10.1021/jo070462w