methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate

Base Information

• Chemical Name: methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate
• CAS No.: 116328-99-5
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 324.374
• Mol file: 116328-99-5.mol

Synonyms:

Chemical Property of methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate

There total 8 articles about methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate 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:

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (3396-71-2) → methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate (116328-99-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 55 percent NaH / 1.) DMF, 25 deg C, 0.5 h; 2.) 25 deg C, 0.5 h

2: 92 percent / 3.2 M aq. HCl / dioxane / 1.25 h / 25 °C

3: 95 percent / tetrahydrofuran / 3.5 h / 25 °C

4: 54 percent / iodine / 2 h / 25 °C

5: 1.) 75 percent OsO₄; 2.) sodium periodate / 1.) aq. dioxane, 23 deg C, 15 min; 2.) 23 deg C, 2.5 h

6: 70 percent K₂CO₃, KHCO₃, KI, I₂ / H₂O; dioxane / 1.75 h / 23 °C

7: diethyl ether

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; iodine; sodium hydride; potassium carbonate; potassium hydrogencarbonate; potassium iodide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water;

DOI:10.1246/bcsj.60.4005

Reference yield:

benzyl bromide (100-39-0) → methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate (116328-99-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 55 percent NaH / 1.) DMF, 25 deg C, 0.5 h; 2.) 25 deg C, 0.5 h

2: 92 percent / 3.2 M aq. HCl / dioxane / 1.25 h / 25 °C

3: 95 percent / tetrahydrofuran / 3.5 h / 25 °C

4: 54 percent / iodine / 2 h / 25 °C

5: 1.) 75 percent OsO₄; 2.) sodium periodate / 1.) aq. dioxane, 23 deg C, 15 min; 2.) 23 deg C, 2.5 h

6: 70 percent K₂CO₃, KHCO₃, KI, I₂ / H₂O; dioxane / 1.75 h / 23 °C

7: diethyl ether

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; iodine; sodium hydride; potassium carbonate; potassium hydrogencarbonate; potassium iodide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water;

DOI:10.1246/bcsj.60.4005

Reference yield:

(3αR,5S,6αR)-5-(benzyloxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (116306-89-9) → methyl (2S,3R,5R)-6-O-benzyl-2,3-O-isopropylidene-2,3,5-trihydroxyhexanoate (116328-99-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / 3.2 M aq. HCl / dioxane / 1.25 h / 25 °C

2: 95 percent / tetrahydrofuran / 3.5 h / 25 °C

3: 54 percent / iodine / 2 h / 25 °C

4: 1.) 75 percent OsO₄; 2.) sodium periodate / 1.) aq. dioxane, 23 deg C, 15 min; 2.) 23 deg C, 2.5 h

5: 70 percent K₂CO₃, KHCO₃, KI, I₂ / H₂O; dioxane / 1.75 h / 23 °C

6: diethyl ether

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; iodine; potassium carbonate; potassium hydrogencarbonate; potassium iodide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water;

DOI:10.1246/bcsj.60.4005

upstream raw materials:

diazomethane

(4S,5R)-5-((S)-3-Benzyloxy-2-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

benzyl bromide

Downstream raw materials:

(4S,5R)-2,2-Dimethyl-5-(2-oxo-ethyl)-[1,3]dioxolane-4-carboxylic acid methyl ester