(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

Base Information

Chemical Name:(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid
CAS No.:676144-83-5
Molecular Formula:C₃₀H₆₃NO₇Si₃
Molecular Weight:634.089
Hs Code.:

Synonyms:(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

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Chemical Property of (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

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Technology Process of (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

There total 10 articles about (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid 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: 93.0%

: 676144-82-4
(1S,4R,5S,6S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-3-oxo-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

: 676144-83-5
(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 24h;
DOI:10.1021/jo0357216

Reference yield:

: 140193-76-6
5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone

: 676144-83-5
(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 3.1 g / NaBH₄ / NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

2: 96 percent / DBU / 12 h / 140 °C

3: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

4: 79 percent / AcOH / H₂O / 7 h / 80 °C

5: 96 percent / pyridine; DMAP / 1 h / 20 °C

6: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -80 - 25 °C

7: 89 percent / DIPEA / CH₂Cl₂ / 2 h / 25 °C

8: 97 percent / NH₃; Na / tetrahydrofuran / 0.5 h / -78 °C

9: 87 percent / DMAP / acetonitrile / 12 h / 20 °C

10: 93 percent / LiOH / tetrahydrofuran; H₂O / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; ammonia; sodium; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 6: Swern oxidation;
DOI:10.1021/jo0357216

Reference yield:

: 227780-31-6
(1'S,4''S,5S)-5-[benzylamino-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-4,5-dihydrofuran-2(3H)-one

: 676144-83-5
(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / DBU / 12 h / 140 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 79 percent / AcOH / H₂O / 7 h / 80 °C

4: 96 percent / pyridine; DMAP / 1 h / 20 °C

5: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -80 - 25 °C

6: 89 percent / DIPEA / CH₂Cl₂ / 2 h / 25 °C

7: 97 percent / NH₃; Na / tetrahydrofuran / 0.5 h / -78 °C

8: 87 percent / DMAP / acetonitrile / 12 h / 20 °C

9: 93 percent / LiOH / tetrahydrofuran; H₂O / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; oxalyl dichloride; ammonia; sodium; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; 5: Swern oxidation;
DOI:10.1021/jo0357216