[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

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Chemical Name:[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester
CAS No.:269715-80-2
Molecular Formula:C₁₉H₃₃NO₄Si
Molecular Weight:367.561
Hs Code.:

Synonyms:[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

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Chemical Property of [(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

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Technology Process of [(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

There total 1 articles about [(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl 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: 89.0%

: 269715-77-7
3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester

: 269715-79-9
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-3-oxo-propyl]-carbamic acid benzyl ester

: 269715-80-2
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃;
DOI:10.1016/S0040-4039(99)02348-5

Reference yield: 91.0%

: 269715-80-2
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

: 269715-79-9
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-3-oxo-propyl]-carbamic acid benzyl ester

Guidance literature:: With Dess-Martin periodane;
DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

: 269715-80-2
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester

: (2aS,3R,4S,5aS,7R)-4-Hydroxy-3,7-dimethyl-2,2a,3,4,5,5a,6,7-octahydro-1,8,8b-triaza-acenaphthylene-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 91 percent / Dess-Martin periodinane

2: 51 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3: 100 percent / 2,6-lutidine

4: 90 percent / Et₃N

5: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

6: 64 percent / LDA / tetrahydrofuran

7: 74 percent / pTSA / benzene / Heating

8: 100 percent / H₂ / Pd/C

9: 85 percent / HgCl₂; Et₃N / dimethylformamide

10: 100 percent / NaBH₄ / methanol

11: 63 percent / PPh₃; DIAD

12: 67 percent / NaH / tetrahydrofuran; methanol

13: 84 percent / TBAF / tetrahydrofuran

14: 27 percent / PPh₃; DIAD

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Oxidation / 2: allylation / 3: Etherification / 4: Acylation / 5: ozonolysis / 6: Wittig reaction / 7: Cyclization / 8: Hydrogenolysis / 9: Substitution / 10: Reduction / 11: Cyclization / 12: Substitution / 13: Substitution / 14: Cyclization;
DOI:10.1016/S0040-4039(99)02348-5