4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal

Base Information

• Chemical Name: 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal
• CAS No.: 121687-41-0
• Molecular Formula: C₃₈H₄₄O₇
• Molecular Weight: 612.763

Synonyms:4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal

Chemical Property of 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal

Chemical Property:

Purity/Quality:

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Technology Process of 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal

There total 2 articles about 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal 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:

4,5,6,8-tetra-O-acetyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal (121687-40-9) → 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal (121687-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.02M NaOCH₃

2: 9.3 g / NaH / dimethylformamide / 5 h

With sodium methylate; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(88)84081-3

Reference yield:

benzyl bromide (100-39-0) + (2R,3R,4S,5S,6R)-2-(1,1-Dimethoxy-ethyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol → 4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal (121687-41-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 5h;

DOI:10.1016/0008-6215(88)84081-3

Reference yield: 88.0%

4,5,6,8-tetra-O-benzyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal (121687-41-0) → 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-D-glycero-D-gulo-2-octulose (121687-36-3)

Guidance literature:

With water; acetic acid; at 65 - 70 ℃; for 2h;

DOI:10.1016/0008-6215(88)84081-3

upstream raw materials:

benzyl bromide

4,5,6,8-tetra-O-acetyl-3,7-anhydro-1-deoxy-D-glycero-D-gulo-2-octulose 2,2-dimethyl acetal

Downstream raw materials:

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-D-glycero-D-gulo-2-octulose

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-2-deuterio-2-O-p-tolylsulfonyl-D-erythro-L-galacto-octilol

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-2-deuterio-2-O-p-tolylsulfonyl-D-erythro-L-talo-octilol

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-2-deuterio-D-erythro-L-talo-octilol

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