(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

Base Information

Chemical Name:(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester
CAS No.:676144-84-6
Molecular Formula:C₃₀H₆₅NO₆Si₃
Molecular Weight:620.106
Hs Code.:

Synonyms:(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

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Chemical Property of (1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

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Technology Process of (1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

There total 11 articles about (1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester 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: 86.0%

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

: 676144-84-6
(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;
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

: 676144-84-6
(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

11: 86 percent / BH₃*Me₂S / tetrahydrofuran / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide borane complex; 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

: 676144-84-6
(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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

10: 86 percent / BH₃*Me₂S / tetrahydrofuran / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; 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