(1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane

Base Information

• Chemical Name: (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane
• CAS No.: 691179-17-6
• Molecular Formula: C₂₉H₃₉NO₁₀S
• Molecular Weight: 593.695
• Mol file: 691179-17-6.mol

Synonyms:(1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane

Chemical Property of (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane

There total 2 articles about (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.0^16,21]tricosane 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: 55.0%

toluene-4-sulfonamide (70-55-3) + methyl 4,6-O-benzylidene-2,3-O-bis[(2-chloroethoxy)ethyl]-α-D-mannopyranoside (691179-04-1) → (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.016,21]tricosane (691179-17-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; Heating;

DOI:10.1055/s-2004-817751

Reference yield:

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.016,21]tricosane (691179-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / sodium hydroxide; tetrabutylammonium hydrogen sulfate / H₂O / 18 h / 20 °C

2: 52 percent / anhydrous potassium crbonate / dimethylformamide / 32 h / Heating

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2005.03.025

Reference yield: 92.0%

(1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-8-(toluene-4-sulfonyl)-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.016,21]tricosane (691179-17-6) → (1S,15S,16R,18R,21R,23S)-23-Methoxy-18-phenyl-2,5,11,14,17,19,22-heptaoxa-8-aza-tricyclo[13.8.0.016,21]tricosane

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; Heating;

DOI:10.1055/s-2004-817751

upstream raw materials:

toluene-4-sulfonamide

methyl 4,6-O-benzylidene-2,3-O-bis[(2-chloroethoxy)ethyl]-α-D-mannopyranoside

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside