methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate

Base Information

• Chemical Name: methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate
• CAS No.: 1392067-05-8
• Molecular Formula: C₂₁H₂₆O₉
• Molecular Weight: 422.432

Synonyms:

Chemical Property of methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate

There total 15 articles about methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate 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:

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside (197577-12-1) → methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate (1392067-05-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

4.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

7.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

9.1: pyridine / methanol / 72 h / 60 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

11.1: sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 0 °C

12.1: acetyl chloride / 0.17 h / 0 °C / Inert atmosphere

12.2: 17.5 h / 0 - 60 °C / Inert atmosphere

13.1: hydrogenchloride / methanol; water / 3.5 h / 20 °C

14.1: pyridine / 16 h / 20 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogen phosphate monohydrate; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo301240j

Reference yield:

(2S,3S,4aR,5R,7S,8S,8aR)-5-(hydroxymethyl)-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-8-ol4 (176897-12-4) → methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate (1392067-05-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / Reflux

2.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

5.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

6.2: 3 h / 0 - 20 °C / Inert atmosphere

7.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

8.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

10.1: pyridine / methanol / 72 h / 60 °C

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

12.1: sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 0 °C

13.1: acetyl chloride / 0.17 h / 0 °C / Inert atmosphere

13.2: 17.5 h / 0 - 60 °C / Inert atmosphere

14.1: hydrogenchloride / methanol; water / 3.5 h / 20 °C

15.1: pyridine / 16 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium chlorite; sodium dihydrogen phosphate monohydrate; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydride; dimethyl sulfoxide; acetyl chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo301240j

Reference yield:

(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside (1252047-54-3) → methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate (1392067-05-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

3.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

6.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

8.1: pyridine / methanol / 72 h / 60 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

10.1: sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 0 °C

11.1: acetyl chloride / 0.17 h / 0 °C / Inert atmosphere

11.2: 17.5 h / 0 - 60 °C / Inert atmosphere

12.1: hydrogenchloride / methanol; water / 3.5 h / 20 °C

13.1: pyridine / 16 h / 20 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogen phosphate monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo301240j

upstream raw materials:

(2S,3S,4aR,5S,7S,8R,8aR)-7-(benzyloxy)-8-hydroxy-2,3-dimethoxy-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside

(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1392067-05-8 methyl 1-O-benzyl-2,3,4-tri-O-acetyl-5a-carba-α-D-mannuronoate

Send

Send

Metric Ton KG G Pound L ML

Send

Send