6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

Base Information

• Chemical Name: 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose
• CAS No.: 118893-79-1
• Molecular Formula: C₂₄H₃₆O₁₁
• Molecular Weight: 500.543

Synonyms:6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

Chemical Property of 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

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-D-glycero-D-galacto-D-galacto-undecapyranose

There total 14 articles about 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose 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,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-D-glycero-D-galacto-D-galacto-undecapyranose (118893-79-1)

Guidance literature:

Multi-step reaction with 13 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

10: 75 percent / MgBr₂ / CH₂Cl₂; toluene / 0 °C

11: 95 percent / NaBH₄, CeCl₃

12: 2.) K₂CO₃ / 2.) CH₃OH

13: LiBH₄ / tetrahydrofuran / Heating

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; borane-THF; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; ozone; acetic acid; triethylamine; magnesium bromide; zinc; sulfuric acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a090

Reference yield:

C26H24O8 (118893-76-8) → 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose (118893-79-1)

Guidance literature:

Multi-step reaction with 14 steps

1: K₂CO₃ / methanol

2: H₂SO₄

3: O₃ / CH₂Cl₂; methanol / -78 °C

4: BH₃*THF

6: BF₃*Et₂O

7: NaH / dimethylformamide

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

9: Et₃N, DMAP / CH₂Cl₂

10: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂

11: 75 percent / MgBr₂ / CH₂Cl₂; toluene / 0 °C

12: 95 percent / NaBH₄, CeCl₃

13: 2.) K₂CO₃ / 2.) CH₃OH

14: LiBH₄ / tetrahydrofuran / Heating

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; borane-THF; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; ozone; acetic acid; triethylamine; magnesium bromide; zinc; sulfuric acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a090

Reference yield:

(3S,4S,5S,6S)-6-[(R)-Benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol (99166-48-0,119007-10-2,119007-11-3) → 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose (118893-79-1)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; Heating;

DOI:10.1021/ja00311a090

upstream raw materials:

(3S,4S,5S,6S)-6-[(R)-Benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol

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

1-[2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydro-di[1,3]dioxolo[5,4-b:5,4-d]pyran-5-yl]-(1R)-but-3-en-1-ol

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

Downstream raw materials:

6,7,8,9,10,11-hexa-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

(2S,3R,4S,5R)-2-((1R,2S,3S,4R,5R)-1,2,3,4,5,6-Hexakis-benzyloxy-hexyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol

methyl 4-azido-6,7,8,9,10,11-hexa-O-benzyl-4-deoxy-D-glycero-D-galacto-α-D-gluco-undecapyranoside

methyl 2,3-di-O-acetyl-4-azido-6,7,8,9,10,11-hexa-O-benzyl-4-deoxy-D-glycero-D-galacto-α-D-gluco-undecapyranoside

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