(2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester
• CAS No.: 676241-09-1
• Molecular Formula: C₆₀H₆₈N₂O₁₁
• Molecular Weight: 993.207
• Mol file: 676241-09-1.mol

Synonyms:(2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Chemical Property of (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

There total 9 articles about (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester 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: 79.0%

(2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester (676241-08-0) → (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester (676241-09-1)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran (112219-66-6) → (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester (676241-09-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 °C

2.1: sodium methylate / methanol / 20 h / 20 °C

3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

4.1: ozone / dichloromethane / 0.5 h / -78 °C

4.2: NaBH₄ / 11; 15 / 20 h / 20 °C

5.1: triethylamine / dichloromethane / 20 h / 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

7.1: trifluoroacetic acid / dichloromethane / 20 h / 20 °C

8.1: diethylphosphoryl cyanide; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C

9.1: water; triphenylphosphine / tetrahydrofuran / 20 h / 20 °C

With sodium azide; diethylphosphoryl cyanide; trimethylsilyl trifluoromethanesulfonate; water; sodium methylate; acetic anhydride; ozone; triethylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Zemplen deacetylation / 9.1: Staudinger reaction;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol (676241-03-5) → (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester (676241-09-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

2.1: ozone / dichloromethane / 0.5 h / -78 °C

2.2: NaBH₄ / 11; 15 / 20 h / 20 °C

3.1: triethylamine / dichloromethane / 20 h / 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

5.1: trifluoroacetic acid / dichloromethane / 20 h / 20 °C

6.1: diethylphosphoryl cyanide; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C

7.1: water; triphenylphosphine / tetrahydrofuran / 20 h / 20 °C

With sodium azide; diethylphosphoryl cyanide; water; acetic anhydride; ozone; triethylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 7.1: Staudinger reaction;

DOI:10.1016/j.tetlet.2003.12.032

upstream raw materials:

(2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

C₁₁₆H₁₂₄N₆O₂₁