(2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester
• CAS No.: 191732-79-3
• Molecular Formula: C₂₁H₂₇NO₅S
• Molecular Weight: 405.515
• Mol file: 191732-79-3.mol

Synonyms:(2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property of (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester

There total 1 articles about (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl 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: 86.0%

benzyl bromide (100-39-0) + ((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester (116611-50-8) → (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester (191732-79-3)

Guidance literature:

((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 ℃; for 24h;

DOI:10.1016/S0040-4039(99)00978-8

Reference yield: 85.0%

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) + (2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester (191732-79-3) → (2S,5S)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol (237388-03-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1016/S0040-4039(99)00978-8

Reference yield:

(2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-carbamic acid tert-butyl ester (191732-79-3) → (4S,5R)-4-Benzyloxymethyl-5-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-oxazolidin-2-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: 85 percent / hexane; tetrahydrofuran / 4 h / -78 - 20 °C

2.1: 77 percent / Na₂HPO₄; Na-Hg / methanol / 3 h / 0 °C

3.1: osmium tetraoxide; NMO; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: NaH / tetrahydrofuran / 4 h / 60 °C

With disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; sodium amalgam; water; sodium hydride; In tetrahydrofuran; methanol; hexane; tert-butyl alcohol; 1.1: Metallation / 1.2: Addition / 2.1: Elimination / 3.1: Oxidation / 4.1: Cyclization;

DOI:10.1039/b001721n

upstream raw materials:

benzyl bromide

((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester

Downstream raw materials:

(2S,5S)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

(E)-(2R,5R)-1-Benzyloxy-2-[(tert-butoxycarbonyl)amino]-5,6-isopropylidenedioxyhex-3-ene

1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-5,6-isopropylidene-L-mannitol

1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-5,6-isopropylidene-L-iditol