(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

Base Information

Chemical Name:(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene
CAS No.:944417-15-6
Molecular Formula:C₅₄H₅₂O₅
Molecular Weight:781.004
Hs Code.:

Synonyms:(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

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Chemical Property of (3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

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Technology Process of (3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

There total 4 articles about (3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene 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: 79.0%

: 944417-14-5
(3R,4R,5S)-1,3,4,5-tetrabenzyloxy-6-trityloxy-2-hexanone

: 2065-66-9
methyl-triphenylphosphonium iodide

: 944417-15-6
(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

Guidance literature:: methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

(3R,4R,5S)-1,3,4,5-tetrabenzyloxy-6-trityloxy-2-hexanone; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Further stages.;
DOI:10.1039/b704509c

Reference yield:

: 6386-24-9
2,3,4,6-tetra-O-benzyl-D-galactopyranose

: 944417-15-6
(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / NaBH₄ / ethanol / 15 h / 20 °C

2.1: 74 percent / pyridine / 72 h / 20 °C

3.1: 86 percent / acetic anhydride; DMSO / 16 h / 20 °C

4.1: nBuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 79 percent / tetrahydrofuran / 16 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; ethanol; 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1039/b704509c

Reference yield:

: 165881-13-0
2,3,4,6-tetra-O-benzyl-1-O-trityl-D-galactitol

: 944417-15-6
(3S,4S,5S)-3,4,5-tribenzyloxy-2-((benzyloxy)methyl)-6-trityloxy-1-hexene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / acetic anhydride; DMSO / 16 h / 20 °C

2.1: nBuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 79 percent / tetrahydrofuran / 16 h / 0 - 20 °C

With n-butyllithium; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1039/b704509c