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

Base Information

• Chemical Name: 6-O-benzyl-1,2:3,4-di-O-isopropylidene-β-L-lyxo-D-galacto-nonopyranose
• CAS No.: 110921-01-2
• Molecular Formula: C₂₂H₃₂O₉
• Molecular Weight: 440.491
• Mol file: 110921-01-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 6-O-benzyl-1,2:3,4-di-O-isopropylidene-β-L-lyxo-D-galacto-nonopyranose 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: 82.5%

(E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-non-7-enopyranose (110921-00-1) → (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 (110921-01-2,110921-02-3)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 3h; Ambient temperature;

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

Reference yield: 71.0%

methyl 6-O-benzyl-1,2:3,4-di-O-isopropilidene-β-L-lyxo-D-galacto-nonopyranuronate (110921-06-7) → 6-O-benzyl-1,2:3,4-di-O-isopropylidene-β-L-lyxo-D-galacto-nonopyranose (110921-01-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

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) → (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 (110921-01-2,110921-02-3)

Guidance literature:

Multi-step reaction with 6 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: 90 percent / benzene / 3 h / Heating

5: 70.5 percent / diisobutylaluminium hydride / CH₂Cl₂ / 2 h / 0 °C

6: 82.5 percent / N-methylmorpholine N-oxide monohydrate, osmium tetraoxide / acetone; H₂O / 3 h / Ambient temperature

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

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

upstream raw materials:

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

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

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

benzyl bromide