5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester)

Base Information

• Chemical Name: 5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester)
• CAS No.: 67109-74-4
• Molecular Formula: C₁₄H₁₉NO₇S
• Molecular Weight: 345.373
• Mol file: 67109-74-4.mol

Synonyms:5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester);GlcNAc-thiazoline triacetate

Chemical Property of 5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester)

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

5-[(Acetyloxy)methyl]-3a,6,7,7a-tetrahydro-2-methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diolDiacetate(Ester) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-[(Acetyloxy)methyl]-3a,6,7,7a-tetrahydro-2-methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester), is an intermediate in the synthesis Hexosaminidase inhibitor derivatives, which are the new drug candidates for the therapy of oste

Technology Process of 5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (Ester)

There total 4 articles about 5-[(Acetyloxy)Methyl]-3a,6,7,7a-tetrahydro-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-Pyrano[3,2-d]thiazole-6,7-diol Diacetate (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: 100.0%

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole (67145-37-3,67109-74-4)

Guidance literature:

With Lawessons reagent; In toluene; at 80 ℃; for 1.5h;

DOI:10.1021/jo010088e DOI:10.1021/ol0269796

Reference yield: 73.0%

6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol (51471-40-0) → (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole (67145-37-3,67109-74-4)

Guidance literature:

With pyridine; trifluorormethanesulfonic acid; iodine; In tetrahydrofuran; at 0 - 20 ℃; for 0.25h;

DOI:10.1016/j.carres.2015.06.004

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole (67145-37-3,67109-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1 h / 0 °C

2: pyridine; trifluorormethanesulfonic acid; iodine / tetrahydrofuran / 0.25 h / 0 - 20 °C

With pyridine; trifluorormethanesulfonic acid; iodine; sodium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.carres.2015.06.004

upstream raw materials:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol

(+)-D-glucosamine hydrochloride

Downstream raw materials:

(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol

(2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4-diyl diacetate

C₁₅H₁₉NO₄S

cyclohexyl 2-acetamido-2-deoxy-1-thio-3,4,6-tri-O-acetyl-α-D-glucopyranoside

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