(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

Base Information

Chemical Name:(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran
CAS No.:845894-43-1
Molecular Formula:C₃₀H₂₈F₂O₄
Molecular Weight:490.547
Hs Code.:

Synonyms:(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

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Chemical Property of (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

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Technology Process of (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

There total 5 articles about (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-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: 95.0%

: 845894-42-0
(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-one

: 75-61-6
dibromodifluoromethane

: 845894-43-1
(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

Guidance literature:: (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-one; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -40 - 20 ℃;

dibromodifluoromethane; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; Heating;
DOI:10.1002/anie.200461244

Reference yield:

: (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-ol

: 845894-43-1
(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: 74 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

2.1: HMPT / tetrahydrofuran / -40 - 20 °C

2.2: 95 percent / HMPT / tetrahydrofuran / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; 4 A molecular sieve; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.200461244

Reference yield:

: 845894-39-5
(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-prop-1-ynyl-tetrahydro-pyran

: 845894-43-1
(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-difluoromethylene-6-prop-1-ynyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / H₂SO₄ / 0.05 h / 0 °C

2.1: 90 percent / MeONa / methanol / 2 h / 0 - 20 °C

3.1: 74 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

4.1: HMPT / tetrahydrofuran / -40 - 20 °C

4.2: 95 percent / HMPT / tetrahydrofuran / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; 4 A molecular sieve; sulfuric acid; sodium methylate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200461244