(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

Base Information

Chemical Name:(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol
CAS No.:248273-47-4
Molecular Formula:C₃₀H₆₅NO₆Si₃
Molecular Weight:620.106
Hs Code.:

(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

Synonyms:(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

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Chemical Property of (1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

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Technology Process of (1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

There total 10 articles about (1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol 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: 85.0%

: 248273-46-3
(1S,2S,3R,4S,5R)-3,4-bis-(tert-butyldimethylsilanyloxy)-6-(tert-butoxycarbonyl)-2-(triethylsilanyloxy)-6-azabicyclo[3.2.1]octan-7-one

: 248273-47-4
(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 5h;
DOI:10.1021/jo000604l

Reference yield:

: 141293-15-4
(1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

: 248273-47-4
(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

Guidance literature:: Multi-step reaction with 10 steps

1: H₂ / Pd/C / tetrahydrofuran

2: 2,6-lutidine / CH₂Cl₂

3: aq. AcOH / 50 °C

4: 2,6-lutidine; Et₃N / CH₂Cl₂ / 50 °C

5: DMAP / acetonitrile

6: aq. AcOH / 20 °C

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8: 60 percent / LDA / tetrahydrofuran / 0.25 h / -80 °C

9: 100 percent / pyridine; DMAP

10: 70 percent / NaBH₄; H₂O / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; water; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile; 7: Swern oxidation;
DOI:10.1021/ol990880q

Reference yield:

: 190430-55-8
(1'S,2R,4R)-2-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

: 248273-47-4
(1S,2R,3S,4R,6R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-(tert-butoxycarbonylamino)-1-O-(triethylsilanyl)-6-(hydroxymethyl)cyclohexane-1,2,3-triol

Guidance literature:: Multi-step reaction with 8 steps

1: aq. AcOH / 50 °C

2: 2,6-lutidine; Et₃N / CH₂Cl₂ / 50 °C

3: DMAP / acetonitrile

4: aq. AcOH / 20 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

6: 60 percent / LDA / tetrahydrofuran / 0.25 h / -80 °C

7: 100 percent / pyridine; DMAP

8: 70 percent / NaBH₄; H₂O / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; water; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; 5: Swern oxidation;
DOI:10.1021/ol990880q