(4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS No.: 222400-56-8
• Molecular Formula: C₂₀H₃₉NO₇Si
• Molecular Weight: 433.618
• Mol file: 222400-56-8.mol

Synonyms:

Chemical Property of (4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

There total 1 articles about (4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane 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:

methanol (67-56-1) + (4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane (260978-83-4) → (4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane (222400-56-8) + Methyl (R)-2-benzyloxymethoxypropanoate (260978-31-2)

Guidance literature:

(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane; With ozone; In methanol; at -78 ℃; for 0.333333h;

With dimethylsulfide; In methanol; at -78 - 20 ℃; for 1h;

methanol; With water; bromine; sodium hydrogencarbonate; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1039/a905772b

Reference yield:

(4S,5S)-4-[(S)-(tert-Butoxycarbonylamino)methoxycarbonylmethyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane (222400-56-8) → (S)-tert-Butoxycarbonylamino-[(4S,5S)-2,2-dimethyl-5-(4-nitro-phenoxycarbonyloxymethyl)-[1,3]dioxolan-4-yl]-acetic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH / tetrahydrofuran / 12 h / 23 °C

2: pyridine / 1 h / 0 °C

With pyridine; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo9822378

upstream raw materials:

methanol

(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane