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

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-prop-1-ynyl-tetrahydro-pyran
CAS No.:845894-39-5
Molecular Formula:C₃₀H₃₂O₅
Molecular Weight:472.581
Hs Code.:

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

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

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

There total 1 articles about (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-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: 75.0%

: 89160-10-1
methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

: 74-88-4
methyl iodide

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

Guidance literature:: methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 0.5h;

With N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃;
DOI:10.1002/anie.200461244

Reference yield: 75.0%

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

: 108-24-7
acetic anhydride

: 845894-40-8
Acetic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-yl ester

Guidance literature:: With sulfuric acid; at 0 ℃; for 0.05h;
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

: (1R,3R,4R,5S,6S)-4,5,6-Tris-benzyloxy-2,2-difluoro-3-((E)-propenyl)-cyclohexanol

Guidance literature:: Multi-step reaction with 6 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

5.1: [Co₂(CO)8] / CH₂Cl₂ / 2 h / 20 °C

5.2: TIBAL / toluene / 2.5 h / 20 °C

5.3: 65 percent / CAN; NEt₃ / acetone / 0.5 h

6.1: H₂ / Pd/CaCO₃ / methanol / 4 h / 20 °C

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