(3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

Base Information

Chemical Name:(3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester
CAS No.:139303-09-6
Molecular Formula:C₂₁H₃₃NO₆Si
Molecular Weight:423.582
Hs Code.:

Synonyms:

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Chemical Property of (3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

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Technology Process of (3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

There total 5 articles about (3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic 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:

: 501-53-1,94274-21-2
benzyl chloroformate

: 139303-09-6
(3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / NH₂OH*HCl, K₂CO₃ / diethyl ether; H₂O / Ambient temperature

2: 1) molecular sieves, (Pr₄N)IO₄, 2) N-methylmorpholine N-oxide hydrate (NMO) / 2) OsO₄, 70percent t-BuOOH, t-BuOH / 1) CH₂Cl₂, 0 deg C, 1 h, 2) acetone, H₂O, room temp., 4 d

3: Amberlist-15 / 36 h / Ambient temperature

With molecular sieve; tetrapropylammonium periodate; Amberlist-15; hydroxylamine hydrochloride; potassium carbonate; 4-methylmorpholine N-oxide; tert.-butylhydroperoxide; osmium(VIII) oxide; tert-butyl alcohol; In diethyl ether; water;
DOI:10.1002/hlca.19910740806

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139303-09-6
(3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / Et₃N, NaI / acetonitrile / 7 h / 50 °C

2: 1) molecular sieves, (Pr₄N)IO₄, 2) N-methylmorpholine N-oxide hydrate (NMO) / 2) OsO₄, 70percent t-BuOOH, t-BuOH / 1) CH₂Cl₂, 0 deg C, 1 h, 2) acetone, H₂O, room temp., 4 d

3: Amberlist-15 / 36 h / Ambient temperature

With molecular sieve; tetrapropylammonium periodate; Amberlist-15; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tert.-butylhydroperoxide; osmium(VIII) oxide; tert-butyl alcohol; In acetonitrile;
DOI:10.1002/hlca.19910740806

Reference yield:

: 3426-71-9
Benzyl N-hydroxycarbamate

: 139303-09-6
(3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-1,3,5-trioxa-6-aza-indene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1) molecular sieves, (Pr₄N)IO₄, 2) N-methylmorpholine N-oxide hydrate (NMO) / 2) OsO₄, 70percent t-BuOOH, t-BuOH / 1) CH₂Cl₂, 0 deg C, 1 h, 2) acetone, H₂O, room temp., 4 d

2: Amberlist-15 / 36 h / Ambient temperature

With molecular sieve; tetrapropylammonium periodate; Amberlist-15; 4-methylmorpholine N-oxide; tert.-butylhydroperoxide; osmium(VIII) oxide; tert-butyl alcohol;
DOI:10.1002/hlca.19910740806