Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester
CAS No.:134357-76-9
Molecular Formula:C₄₀H₄₈O₁₁
Molecular Weight:704.815
Hs Code.:

Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

There total 37 articles about Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester 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: 54.0%

: 134311-51-6
Acetic acid (2R,3R,4R,5R,6R)-2-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-4-yl ester

: 134311-95-8
Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

: 134311-49-2,134357-75-8,134357-76-9
Acetic acid (2R,3R,4S,5R,6R)-3-((2S,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

: 134357-75-8
Acetic acid (2R,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; 1.) -20 deg C, 2 h, 2.) rt, 5 h;

Reference yield: 53.0%

: 134311-89-0
Acetic acid (2S,3R,4R,5R,6R)-2-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-4-yl ester

: 134311-95-8
Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

: 134357-76-9
Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 0.5h;

Reference yield:

: 20316-77-2
(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 134311-49-2,134357-75-8,134357-76-9
Acetic acid (2R,3R,4S,5R,6R)-3-((2S,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / 2 N H₂SO₄ / methanol / 20 h / Ambient temperature

2: 89 percent / DMAP / CH₂Cl₂; pyridine / 96 h / Ambient temperature

3: 86 percent / LiAlH₄ / tetrahydrofuran / 8 h / Ambient temperature

4: 92 percent / 0.35 M HCl / 96 h / Ambient temperature

5: 33 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

6: t-BuOK / dimethylsulfoxide / 0.33 h / 100 °C

7: 2 N H₂SO₄ / tetrahydrofuran / 24 h / Ambient temperature

8: 95 percent / DMAP / pyridine / 0.33 h / Ambient temperature

9: 89 percent / SOCl₂, AcCl / 16 h / 45 °C

10: 98 percent / H₂O, Ag₂O, BaCO₃ / acetonitrile / 4 h / 45 °C

11: 36 percent / KF, 18-crown-6, Et₃N / tetrahydrofuran / 3 h / Ambient temperature

12: 5 percent / BF₃*OEt₂, activated 4A molecular sieves / CH₂Cl₂ / 1.) -20 deg C, 2 h, 2.) rt, 5 h

With hydrogenchloride; dmap; potassium fluoride; lithium aluminium tetrahydride; thionyl chloride; 18-crown-6 ether; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; potassium tert-butylate; water; potassium hydride; triethylamine; acetyl chloride; barium carbonate; silver(l) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile;