Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate

Base Information

• Chemical Name: Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate
• CAS No.: 131541-27-0
• Molecular Formula: C₁₈H₂₉NO₆Si
• Molecular Weight: 383.517
• Mol file: 131541-27-0.mol

Synonyms:

Chemical Property of Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate

There total 3 articles about Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate 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:

benzyl chloroformate (501-53-1,94274-21-2) → Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate (131541-27-0)

Guidance literature:

Multi-step reaction with 2 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

With molecular sieve; tetrapropylammonium periodate; 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:

tert-butyldimethylsilyl chloride (18162-48-6) → Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate (131541-27-0)

Guidance literature:

Multi-step reaction with 2 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

With molecular sieve; tetrapropylammonium periodate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tert.-butylhydroperoxide; osmium(VIII) oxide; tert-butyl alcohol; In acetonitrile;

DOI:10.1002/hlca.19910740806

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) + trans-1-(tert-butyldimethylsiloxy)butadiene (109987-02-2,88346-87-6) → Benzyl r-3-<<(tert-Butyl)dimethylsilyl>oxy>-t-4,t-5-dihydroxy-1,2-oxazinane-2-carboxylate (131507-69-2) + Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate (131541-27-0)

Guidance literature:

With molecular sieve; tetrapropylammonium periodate; 4-methylmorpholine N-oxide; tert.-butylhydroperoxide; osmium(VIII) oxide; tert-butyl alcohol; Yield given. Multistep reaction. Yields of byproduct given; 1) CH₂Cl₂, 0 deg C, 1 h, 2) acetone, H₂O, room temp., 4 d;

DOI:10.1002/hlca.19910740806

upstream raw materials:

Benzyl N-hydroxycarbamate

trans-1-(tert-butyldimethylsiloxy)butadiene

tert-butyldimethylsilyl chloride

benzyl chloroformate

Downstream raw materials:

cis-3,4-dihydroxy-pyrrolidine

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

Benzyl t-6-Hydroxy-r-4,c-5-(isopropylidenedioxy)-1,2-oxazinane-2-carboxylate