1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose
• CAS No.: 171499-89-1
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543
• Mol file: 171499-89-1.mol

Synonyms:1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose

Chemical Property of 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose

There total 4 articles about 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose 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: 90.0%

benzyl bromide (100-39-0) + 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose (161302-88-1) → 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose (171499-89-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

DOI:10.1016/j.bmc.2003.12.040

Reference yield:

(1R,2S,3R,4S,5R)-2-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]octane-4-carbaldehyde → 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose (171499-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.57 g / NaBH₄ / tetrahydrofuran; propan-2-ol / 1 h / 0 °C

2: 90 percent / NaH / dimethylformamide / 4 h / 0 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.bmc.2003.12.040

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → 1,6-anhydro-3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-β-D-glucopyranose (171499-89-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / tetrahydrofuran / 4 h / Heating

2: OsO₄; NaIO₄ / dioxane; H₂O / 1 h

3: 0.57 g / NaBH₄ / tetrahydrofuran; propan-2-ol / 1 h / 0 °C

4: 90 percent / NaH / dimethylformamide / 4 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.bmc.2003.12.040

upstream raw materials:

benzyl bromide

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-vinyl-β-D-glucopyranose

Downstream raw materials:

methyl 3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-α-D-glucopyranoside