1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

Base Information

Chemical Name:1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose
CAS No.:1314746-21-8
Molecular Formula:C₄₆H₅₁N₃O₉Si
Molecular Weight:818.011
Hs Code.:

Synonyms:1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

There total 16 articles about 1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose 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: 92.0%

: 1,6-anhydro-4-O-(2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

: 1314746-21-8
1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

Guidance literature:: 1,6-anhydro-4-O-(2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-L-idopyranose; With sodium methylate; In methanol; at 20 ℃; for 3h; Inert atmosphere;

In methanol; Inert atmosphere;

Reference yield: 63.0%

: 1314746-13-8
1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

: 1314746-21-8
1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

Guidance literature:: 1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-methylaniline; johnphos; sodium t-butanolate; In toluene; at 80 ℃; for 5h;

With tin(IV) chloride; In dichloromethane; for 0.166667h;
DOI:10.1038/nchem.1073

Reference yield:

: p-methylphenyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside

: 1314746-21-8
1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide

2.1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 4 h / -78 - -20 °C

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-methylaniline; johnphos; sodium t-butanolate / toluene / 5 h / 80 °C

3.2: 0.17 h

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydride; N-methylaniline; johnphos; sodium t-butanolate; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1038/nchem.1073