(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

Base Information

Chemical Name:(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide
CAS No.:344615-48-1
Molecular Formula:C₄₅H₆₂N₄O₇Si₂
Molecular Weight:827.181
Hs Code.:

(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

Synonyms:(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

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Chemical Property of (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

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Technology Process of (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

There total 14 articles about (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide 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:

: 500783-41-5
2-azido-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-5-oxo-hexanoic acid methylamide

: 344615-48-1
(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

: 128241-14-5
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

: 344615-48-1
(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 76 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

2.1: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 1.8-diazabicyclo[5.4.0]undec-7-ene / dimethylsulfoxide / 3 h / 0 °C

4.1: NaN₃; 15-crown-5; hexamethylphosphoric triamide / 17 h / 70 °C

5.1: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

6.1: imidazole / dimethylformamide / 17 h / 20 - 60 °C

7.1: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

8.1: imidazole / dimethylformamide / 2 h / 0 °C

9.1: 13.9 g / NaH / dimethylformamide / 5 h / -23 °C

10.1: [Ir(C₈H₁₂)(MePPh₂)2]PF₆ / tetrahydrofuran / 2.5 h / 20 °C

10.2: 82 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / 0 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.03 h / 20 °C

12.1: 1.85 g / methanol / 1.5 h / 20 °C

13.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

14.1: 1.38 g / L-selectride / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 15-crown-5; camphor-10-sulfonic acid; L-Selectride; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Swern oxidation / 13.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 228565-56-8
allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

: 344615-48-1
(2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 1.8-diazabicyclo[5.4.0]undec-7-ene / dimethylsulfoxide / 3 h / 0 °C

3.1: NaN₃; 15-crown-5; hexamethylphosphoric triamide / 17 h / 70 °C

4.1: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

5.1: imidazole / dimethylformamide / 17 h / 20 - 60 °C

6.1: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

7.1: imidazole / dimethylformamide / 2 h / 0 °C

8.1: 13.9 g / NaH / dimethylformamide / 5 h / -23 °C

9.1: [Ir(C₈H₁₂)(MePPh₂)2]PF₆ / tetrahydrofuran / 2.5 h / 20 °C

9.2: 82 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / 0 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.03 h / 20 °C

11.1: 1.85 g / methanol / 1.5 h / 20 °C

12.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

13.1: 1.38 g / L-selectride / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 15-crown-5; camphor-10-sulfonic acid; L-Selectride; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 12.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)01058-X