(2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol
• CAS No.: 500783-40-4
• Molecular Formula: C₃₉H₅₅N₃O₆Si₂
• Molecular Weight: 718.053

Synonyms:

Chemical Property of (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

There total 7 articles about (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol 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:

tert-butyldimethylsilyl chloride (18162-48-6) + allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside (344615-44-7) → (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol (500783-40-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(01)00246-5 DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside (128241-14-5) → (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol (500783-40-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 76 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

2: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

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

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

5: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

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

7: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

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

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; 15-crown-5; camphor-10-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 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) → (2R,3S,4R,5S,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol (500783-40-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: 1.8-diazabicyclo[5.4.0]undec-7-ene / dimethylsulfoxide / 3 h / 0 °C

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

4: 30.7 g / NaBH₄ / methanol / 1.5 h / 0 °C

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

6: 15.8 g / camphorsulfonic acid / methanol; tetrahydrofuran / 26 h / 20 °C

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

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium azide; 15-crown-5; camphor-10-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

allyl 2-azido-3-O-benzyl-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-α-D-mannopyranoside

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:

2-azido-3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-C-(tert-butyldiphenylsilyloxymethyl)-2-deoxy-4-O-(p-methoxybenzyl)-α-D-mannopyranoside

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

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

(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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