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

Base Information

• Chemical Name: (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide
• CAS No.: 344615-49-2
• Molecular Formula: C₅₁H₇₆N₄O₈Si₃
• Molecular Weight: 957.443
• Mol file: 344615-49-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]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: 85.0%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-4-(p-methoxybenzyloxy)hexanoamide (344615-48-1) → (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide (344615-49-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 60 ℃; for 4h;

DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside (128241-14-5) → (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide (344615-49-2)

Guidance literature:

Multi-step reaction with 15 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

15.1: 85 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 4 h / 60 °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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 13.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (228565-56-8) → (2S,3R,4R,5S)-N-methyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide (344615-49-2)

Guidance literature:

Multi-step reaction with 14 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

14.1: 85 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 4 h / 60 °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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 12.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01058-X

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

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

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

allyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

Downstream raw materials:

(2S,3R,4R,5S)-N,N-dimethyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide