1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Base Information

• Chemical Name: 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose
• CAS No.: 215381-41-2
• Molecular Formula: C₃₅H₃₆O₆
• Molecular Weight: 552.667
• Mol file: 215381-41-2.mol

Synonyms:1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Chemical Property of 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

There total 6 articles about 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose 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: 85.0%

ethyl 2,3,4,7-tetra-O-benzyl-1-thio-6-O-trimethylsilyl-L-glycero-α-D-manno-heptopyranoside (215381-15-0) → 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (215381-41-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; for 0.416667h;

DOI:10.1021/jo9808573

Reference yield: 25.0%

2,3,4,6,7-penta-O-benzyl-L-glycero-D-manno-heptopyranosyl N-phenyltrifluoroacetimidate (1520094-87-4) + methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside (1520094-73-8) → methyl (2,3,4,6,7-penta-O-benzyl-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside + 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (215381-41-2)

Guidance literature:

With t-butyldimethylsiyl triflate; In dichloromethane; at 20 ℃; for 3.5h; Molecular sieve; Inert atmosphere;

DOI:10.1021/jo402312x

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (215381-41-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / Mg, HgBr₂ / tetrahydrofuran / 20 - 24 °C

2: 83 percent / pyridine / 1.5 h / Ambient temperature

3: 85 percent / NIS, TfOH / CH₂Cl₂; diethyl ether / 0.42 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; magnesium; mercury dibromide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo9808573

upstream raw materials:

ethyl 2,3,4,7-tetra-O-benzyl-1-thio-6-O-trimethylsilyl-L-glycero-α-D-manno-heptopyranoside

Benzyloxymethyl chloride

ethyl 2,3,4,7-tetra-O-benzyl-1-thio-L,D-glycero-α-D-manno-heptopyranoside

2,3,4,6,7-penta-O-benzyl-L-glycero-D-manno-heptopyranosyl N-phenyltrifluoroacetimidate

Downstream raw materials:

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-3-O-benzoyl-L-glycero-β-D-manno-heptopyranose

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-β-D-manno-heptopyranose

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose