(R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid

Base Information

• Chemical Name: (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid
• CAS No.: 87173-13-5
• Molecular Formula: C₂₅H₂₉NO₈
• Molecular Weight: 471.507
• Mol file: 87173-13-5.mol

Synonyms:(R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid

Chemical Property of (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid

There total 5 articles about (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid 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: 77.0%

(S)-2-chloropropanoic acid (29617-66-1) + N-((2R,4aR,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide → (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid (87173-13-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1021/acs.joc.0c01852

Reference yield:

(S)-2-bromopropanoic acid (32644-15-8,10327-08-9) + N-((2R,4aR,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide → (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid (87173-13-5)

Guidance literature:

N-((2R,4aR,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

(S)-2-bromopropanoic acid; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1039/c4ob02147a

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid (87173-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / benzene / 80 °C / Dean-Stark

2.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / N,N-dimethyl-formamide; 1,4-dioxane / 60 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 0 - 20 °C

With sodium hydride; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In 1,4-dioxane; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c4ob02147a

upstream raw materials:

(S)-2-bromopropanoic acid

N-Acetyl-D-glucosamine

benzyl alcohol

benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside

Downstream raw materials:

O¹-benzyl-O⁴,O⁶-(R)-benzylidene-β-muramic acid lactam

O¹-benzyl-O⁴-acetyl-β-muramic acid lactam

O⁶-acetyl-O¹-benzyl-β-muramic acid lactam

O¹-benzyl-O⁴-acetyl-O⁶-trityl-β-muramic acid lactam