(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

Base Information

Chemical Name:(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene
CAS No.:1184705-55-2
Molecular Formula:C₃₈H₄₃NO₄
Molecular Weight:577.764
Hs Code.:

Synonyms:(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

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Chemical Property of (3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

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Technology Process of (3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

There total 7 articles about (3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene 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:

: 214068-17-4
methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside

: 1184705-86-9
(3R,4S,5S,6S)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

: 1184705-55-2
(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 °C

1.2: 0 - 20 °C

2.1: methanol; sulfuric acid / 3.25 h / 20 °C

3.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

3.2: 67 °C

4.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 40 °C / Sonication

4.2: 1 h / 40 °C

4.3: 1.42 h / 40 °C / Sonication

With 1H-imidazole; methanol; chloro-trimethyl-silane; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1002/ejoc.200900310

Reference yield:

: methyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside

: 1184705-86-9
(3R,4S,5S,6S)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

: 1184705-55-2
(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: methanol; sulfuric acid / 3.25 h / 20 °C

2.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

2.2: 67 °C

3.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 40 °C / Sonication

3.2: 1 h / 40 °C

3.3: 1.42 h / 40 °C / Sonication

With 1H-imidazole; methanol; chloro-trimethyl-silane; sulfuric acid; triphenylphosphine; zinc; In tetrahydrofuran; toluene;
DOI:10.1002/ejoc.200900310

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1184705-86-9
(3R,4S,5S,6S)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

: 1184705-55-2
(3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / acetonitrile / 16 h / 82 °C / Soxhlet apparatus; Molecular sieve

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 °C

2.2: 0 - 20 °C

3.1: methanol; sulfuric acid / 3.25 h / 20 °C

4.1: 1H-imidazole; triphenylphosphine / toluene / Co-concentrating

4.2: 67 °C

5.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 40 °C / Sonication

5.2: 1 h / 40 °C

5.3: 1.42 h / 40 °C / Sonication

With 1H-imidazole; methanol; chloro-trimethyl-silane; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/ejoc.200900310