Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 509085-99-8
• Molecular Formula: C₃₄H₄₂N₂O₇Si
• Molecular Weight: 618.802
• Mol file: 509085-99-8.mol

Synonyms:

Chemical Property of Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl 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:

2-Diazo-3-oxo-butyric acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester → Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (509085-99-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 5h;

DOI:10.1016/S0040-4039(02)02407-3

Reference yield:

2-(trimethylsilyl)ethyl β-D-galactopyranoside (117252-95-6) → Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (509085-99-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / n-Bu₂SnO / benzene / 2 h / 80 °C

2: 67 percent / NaH / dimethylformamide / 14 h

3: 82 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 4.5 h

4: NEt₃ / tetrahydrofuran / 14 h

5: MsN₃; NEt₃ / tetrahydrofuran / 14 h

6: LiOH / tetrahydrofuran; H₂O / 5 h

With lithium hydroxide; ammonium cerium(IV) nitrate; sodium hydride; di(n-butyl)tin oxide; triethylamine; Methanesulfonyl azide; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(02)02407-3

Reference yield:

2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (143571-58-8) → Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester (509085-99-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / tetrahydrofuran / 14 h

2: MsN₃; NEt₃ / tetrahydrofuran / 14 h

3: LiOH / tetrahydrofuran; H₂O / 5 h

With lithium hydroxide; triethylamine; Methanesulfonyl azide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(02)02407-3

upstream raw materials:

2-(trimethylsilyl)ethyl β-D-galactopyranoside

2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

{2-[(2R,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-trimethyl-silane

2-(trimethylsilyl)ethyl 3-O-p-methoxybenzyl-β-D-galactopyranoside