Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 101981-23-1
• Molecular Formula: C₂₉H₃₉N₃O₁₃
• Molecular Weight: 637.641
• Mol file: 101981-23-1.mol

Synonyms:

Chemical Property of Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-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:

Benzyl-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-mannopyranosyl)-α-L-rhamnopyranosid (101981-41-3) → Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester (101981-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂O, CF₃COOH / CH₂Cl₂ / 0.08 h / 0 °C

2: p-toluenesulfonic acid / toluene / 0.5 h / Ambient temperature

With water; trifluoroacetic acid; toluene-4-sulfonic acid; In dichloromethane; toluene;

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester (101981-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 27 percent / silver silicate

2: H₃O(+)

With oxonium; silver silicate;

DOI:10.1016/S0040-4039(00)95120-7

Reference yield:

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide (95451-93-7) → Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2-ethoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester (101981-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 27 percent / silver silicate

2: H₃O(+)

With oxonium; silver silicate;

DOI:10.1016/S0040-4039(00)95120-7

upstream raw materials:

Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((2S,3R,4S,5R,6R)-6-benzyloxy-4,5-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-((3aR,4R,6S,7S,7aR)-4-benzyloxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide

Downstream raw materials:

Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-6-((2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-azido-tetrahydro-pyran-4-yl ester

Benzyl-O-(2-acetamido-2-desoxy-β-D-mannopyranosyl)-(1->4)-O-<(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)>-α-L-rhamnopyranosid

Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-mannopyranosyl)-(1->4)-2-O-acetyl-O-<(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)>-α-L-rhamnopyranosid

Benzyl-2-O-acetyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->3)-O-<(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-mannopyranosyl)-(1->4)>-α-L-rhamnopyranosid