methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside

Base Information

• Chemical Name: methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside
• CAS No.: 74072-32-5
• Molecular Formula: C₁₃H₂₂O₇
• Molecular Weight: 290.313
• Mol file: 74072-32-5.mol

Synonyms:methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside

Chemical Property of methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside

There total 1 articles about methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside 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: 83.0%

methyl 2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside (74072-30-3) + L-2-chloropropionic acid (598-78-7,7474-05-7,29617-66-1,62138-52-7) → methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside (74072-32-5)

Guidance literature:

With sodium hydride; In 1,4-dioxane; 1.) 1.5 h, 95 deg C, 2.) 3 h, 65 deg C;

DOI:10.1016/S0008-6215(00)80680-1

Reference yield:

methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside (74072-32-5) → 2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-D-arabino-hexopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dicyclohexylcarbodiimide, N-hydroxysuccinimide; 2.) triethylamine / 1.) 1,4-dioxane; 2.) 1,4-dioxane

2: 45 mg / 80 percent aq. trifluoroacetic acid / 7 h / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;

DOI:10.1016/S0008-6215(00)80680-1

Reference yield:

γ-benzyl ester of trifluoroacetyl-L-alanyl-D-isoglutamine (80935-24-6) + methyl 3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside (74072-32-5) → methyl 2-deoxy-5,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-D-arabino-hexofuranoside (81086-83-1)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) 1,4-dioxane; 2.) 1,4-dioxane;

DOI:10.1016/S0008-6215(00)80680-1

upstream raw materials:

methyl 2-deoxy-5,6-O-isopropylidene-D-arabino-hexofuranoside

L-2-chloropropionic acid

Downstream raw materials:

methyl 2-deoxy-5,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-D-arabino-hexofuranoside

(R)-4-Carbamoyl-4-((S)-2-{(R)-2-[(2S,3R)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-tetrahydro-furan-3-yloxy]-propionylamino}-propionylamino)-butyric acid benzyl ester