(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran
CAS No.:139195-27-0
Molecular Formula:C₃₆H₃₆Br₂O₅
Molecular Weight:708.487
Hs Code.:

Synonyms:(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

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Chemical Property of (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

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Technology Process of (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

There total 1 articles about (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran 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:

: 79258-16-5
2,6-anhydro-1,3,4,5-tetra-O-benzyl-D-glycero-L-gulo-heptitol

: 139195-27-0
(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: DMSO, (COCl)2, NEt₃ / CH₂Cl₂

2: 1.) Ph₃P / 1.) CH₂Cl₂, room temperature, 20 min, 2.) CH₂Cl₂, a) 0 deg C, 5 min, b) room temperature, 25 min

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane;
DOI:10.1021/jo00022a039

Reference yield: 89.0%

: 139195-27-0
(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

: 139195-28-1
(2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -80 ℃; for 0.166667h;
DOI:10.1021/jo00022a039

Reference yield:

: 139195-27-0
(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran

: 139195-33-8,139242-04-9
(Z)-(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / n-BuLi / tetrahydrofuran / 0.17 h / -80 °C

2: 97 percent / iodine, morpholine / benzene / 24 h / 45 °C

3: 77 percent / potassium azodicarboxylate, acetic acid / dioxane / 5 h / Ambient temperature

4: 67 percent / 0.11percent NiCl₂/CrCl₂ / dimethylsulfoxide / 168 h / Ambient temperature

With morpholine; chromium dichloride; n-butyllithium; iodine; potassium diazodicarboxylate; acetic acid; nickel dichloride; In tetrahydrofuran; 1,4-dioxane; dimethyl sulfoxide; benzene;
DOI:10.1021/jo00022a039