tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate

Base Information

• Chemical Name: tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate
• CAS No.: 1352051-39-8
• Molecular Formula: C₂₁H₂₉NO₄
• Molecular Weight: 359.466
• Mol file: 1352051-39-8.mol

Synonyms:tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate

Chemical Property of tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate

There total 1 articles about tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate 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:

di-tert-butyl dicarbonate (24424-99-5) + benzaldehyde dimethyl acetal (1125-88-8) + 1-amino-2-propene (107-11-9,30551-89-4) + ((2S,3S)-3-allyloxiran-2-yl)methanol (353490-93-4) → tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate (1352051-39-8) + tert-butyl allyl((1R)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)but-3-en-1-yl)carbamate (1352051-38-7)

Guidance literature:

1-amino-2-propene; ((2S,3S)-3-allyloxiran-2-yl)methanol; With lithium perchlorate; In acetonitrile; at 20 ℃; for 10h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In methanol; for 16h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 10h; regioselective reaction;

DOI:10.1016/j.tetasy.2011.10.008

Reference yield: 96.0%

tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate (1352051-39-8) → (4aR,9aS)-tert-butyl 2-phenyl-4,4a,9,9a-tetrahydro-[1,3]dioxino[5,4-b]azepine-5(6H)-carboxylate (1352051-43-4)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 8h;

DOI:10.1016/j.tetasy.2011.10.008

Reference yield:

tert-butyl allyl((4S,5R)-4-allyl-2-phenyl-1,3-dioxan-5-yl)carbamate (1352051-39-8) → (4aR,7R,8S,9aS)-tert-butyl 7,8-dihydroxy-2-phenylhexahydro-[1,3]dioxino[5,4-b]azepine-5(6H)-carboxylate (1352051-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Grubbs catalyst first generation / dichloromethane / 8 h / 40 °C

2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 5 h / 20 °C

With Grubbs catalyst first generation; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In dichloromethane; acetone;

DOI:10.1016/j.tetasy.2011.10.008

upstream raw materials:

di-tert-butyl dicarbonate

benzaldehyde dimethyl acetal

1-amino-2-propene

((2S,3S)-3-allyloxiran-2-yl)methanol

Downstream raw materials:

(4aR,9aS)-tert-butyl 2-phenyl-4,4a,9,9a-tetrahydro-[1,3]dioxino[5,4-b]azepine-5(6H)-carboxylate

(4aR,7R,8S,9aS)-tert-butyl 7,8-dihydroxy-2-phenylhexahydro-[1,3]dioxino[5,4-b]azepine-5(6H)-carboxylate