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

Base Information

• Chemical Name: 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose
• CAS No.: 91860-98-9
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.45
• Mol file: 91860-98-9.mol

Synonyms:6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose

Chemical Property of 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose

There total 10 articles about 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose 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:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose (91860-98-9)

Guidance literature:

Multi-step reaction with 2 steps

2: NaH

With sodium hydride;

DOI:10.1016/S0040-4020(01)90570-8

Reference yield:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) + vinyl magnesium bromide (1826-67-1) + benzyl bromide (100-39-0) → 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose (91860-98-9) + 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-oct-7-enopyranose (91860-99-0)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 0 deg C, 0.5 h, room temp. 6.5 h; 2.) THF, 16 h;

DOI:10.1021/ja00291a027

Reference yield:

benzyl bromide (100-39-0) → 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose (91860-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH

2: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C; 2.) room temp., 90 min

3: 185 mg / NaBH₄ / CH₂Cl₂; ethanol / 0.5 h / 0 °C

4: 1.) o-nitrophenyl selenocyanate, n-butylphosphine; 2.) H₂O₂ (30percent) / 1.) THF, 30 min, room temp.; 2.) 0 deg C, 1 h; room temp., 6h

With sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; n-butylphosphine; dihydrogen peroxide; sodium hydride; ozone; acetic acid; zinc; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)90570-8

upstream raw materials:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

vinyl magnesium bromide

benzyl bromide

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

Downstream raw materials:

(2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one

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

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

(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