(2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol

Base Information

• Chemical Name: (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol
• CAS No.: 1375103-20-0
• Molecular Formula: C₄₅H₅₅N₃O₉
• Molecular Weight: 781.946

Synonyms:(2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol

Chemical Property of (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol

There total 6 articles about (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol 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:

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran (4291-68-3,25320-59-6,41110-63-8,67068-83-1,67773-44-8,69237-96-3,92470-93-4,93601-69-5,113829-62-2) + (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1,3,4-nonanetriol (1391849-30-1) → (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-β-D-galactosyl)-1,3,4-nonanetriol + (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol (1375103-20-0) + methyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside (195827-82-8)

Guidance literature:

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran; (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1,3,4-nonanetriol; With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; In toluene; at 20 - 80 ℃; for 60.75h; Inert atmosphere; Molecular sieve;

With methanol; at 50 ℃; for 6h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.bmc.2012.03.025

Reference yield:

4,5-anhydro-1,3-O-benzylidene-D-arabinitol (164576-09-4) → (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-β-D-galactosyl)-1,3,4-nonanetriol + (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol (1375103-20-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / 0.08 h / 0 °C

1.2: 20 h / 0 - 20 °C

2.1: pyridine / 36 h / 0 - 20 °C

3.1: 20 % Pd(OH)2/C; hydrogen / ethanol / 1.5 h / 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 3 h / 95 °C

5.1: toluene-4-sulfonic acid / 21 h / 0 °C

6.1: tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine / toluene / 60.75 h / 20 - 80 °C / Inert atmosphere; Molecular sieve

6.2: 6 h / 50 °C / Inert atmosphere

With pyridine; sodium azide; 20 % Pd(OH)2/C; tetrabutylammomium bromide; hydrogen; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2012.03.025

Reference yield:

C15H22O5 (1375103-41-5) → (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-β-D-galactosyl)-1,3,4-nonanetriol + (2S,3S,4R)-2-azido-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1,3,4-nonanetriol (1375103-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 36 h / 0 - 20 °C

2.1: 20 % Pd(OH)2/C; hydrogen / ethanol / 1.5 h / 20 °C

3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 95 °C

4.1: toluene-4-sulfonic acid / 21 h / 0 °C

5.1: tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine / toluene / 60.75 h / 20 - 80 °C / Inert atmosphere; Molecular sieve

5.2: 6 h / 50 °C / Inert atmosphere

With pyridine; sodium azide; 20 % Pd(OH)2/C; tetrabutylammomium bromide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2012.03.025

upstream raw materials:

C₈H₁₇N₃O₄

C₁₅H₂₂O₅

C₉H₂₀O₇S

(2R,3R,4R)-1,3-O-(S)-benzylidene-2-O-methanesulfonyl-6-oxa-1,2,3,4-nonanetetrol

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