methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate

Base Information

• Chemical Name: methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate
• CAS No.: 110921-05-6
• Molecular Formula: C₂₃H₃₀O₈
• Molecular Weight: 434.486
• Mol file: 110921-05-6.mol

Synonyms:methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate

Chemical Property of methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate

There total 5 articles about methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate 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: 75.0%

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate (110921-05-6)

Guidance literature:

In methanol; at 4 ℃; for 20h;

DOI:10.1016/0008-6215(86)84007-1

Reference yield:

7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-hept-7-enopyranose (4640-86-2) → methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate (110921-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium hydride / 1.) tetrahydrofuran, 30 min, 2.) r.t.

2: 92 g / N-methylmorpholine N-oxide monohydrate, osmium tetraoxide / acetone; H₂O / 3 h / Ambient temperature

3: 2.93 g / sodium periodate / dioxane; H₂O / 2 h / Ambient temperature

4: 75 percent / methanol / 20 h / 4 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In 1,4-dioxane; methanol; water; acetone;

DOI:10.1016/0008-6215(86)84007-1

Reference yield:

benzyl bromide (100-39-0) → methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranuronate (110921-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium hydride / 1.) tetrahydrofuran, 30 min, 2.) r.t.

2: 92 g / N-methylmorpholine N-oxide monohydrate, osmium tetraoxide / acetone; H₂O / 3 h / Ambient temperature

3: 2.93 g / sodium periodate / dioxane; H₂O / 2 h / Ambient temperature

4: 75 percent / methanol / 20 h / 4 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In 1,4-dioxane; methanol; water; acetone;

DOI:10.1016/0008-6215(86)84007-1

upstream raw materials:

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose

methyl (triphenylphosphoranylidene)acetate

7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-hept-7-enopyranose

benzyl bromide

Downstream raw materials:

(R)-4-Benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-butane-1,2,3-triol

6-O-benzyl-1,2:3,4-di-O-isopropylidene-β-L-lyxo-D-galacto-nonopyranose

methyl 6-O-benzyl-1,2:3,4-di-O-isopropilidene-β-L-lyxo-D-galacto-nonopyranuronate

methyl 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-xylo-D-galacto-nonopyranuronate