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

Base Information

• Chemical Name: 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose
• CAS No.: 91861-00-6
• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.422
• Mol file: 91861-00-6.mol

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

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

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-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose

There total 28 articles about 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose 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: 61.0%

[(R)-2-Benzyloxy-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-eth-(E)-ylidene]-pyrrolidin-1-yl-amine (182298-43-7) → 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6)

Guidance literature:

With 2,3-dimercapto-succinic acid; ozone;

DOI:10.1016/0040-4039(96)01226-9

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-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / CH₂Cl₂ / 15 h / Ambient temperature

2: 84 percent / NaH, TBAI / tetrahydrofuran

3: 61 percent / O₃, DMS

With 2,3-dimercapto-succinic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(96)01226-9

Reference yield:

(3aR,5S,6R,7S,7aR)-5-Furan-2-yl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (118893-77-9) → 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose (91861-00-6)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂SO₄

2: O₃ / CH₂Cl₂; methanol / -78 °C

3: BH₃*THF

5: BF₃*Et₂O

6: NaH / dimethylformamide

7: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C

8: Et₃N, DMAP / CH₂Cl₂

9: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂

With dmap; borane-THF; boron trifluoride diethyl etherate; sodium hydride; ozone; acetic acid; triethylamine; zinc; sulfuric acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00311a090

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

(6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

(6S)-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

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

Downstream raw materials:

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

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