(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

Base Information

Chemical Name:(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol
CAS No.:98003-91-9
Molecular Formula:C₁₈H₂₈O₆
Molecular Weight:340.417
Hs Code.:

Synonyms:(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

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Chemical Property of (2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

Chemical Property:

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Technology Process of (2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

There total 14 articles about (2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol 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:

: 35784-67-9,53270-26-1,53929-07-0,53929-16-1,64696-56-6
1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-glucofuranose

: 98003-91-9
(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / NaH / dimethylsulfoxide

2: 87 percent / 2percent H₂SO₄ / methanol

3: 61 percent / Pb(OAc)4 / benzene

4: 90 percent / diethyl ether / diastereomers ratio 4:1

5: 91 percent / PCC, mol.sieve / CH₂Cl₂

6: 89 percent / K₂CO₃ / methanol

7: 100 percent / Hydrogen / Pd/C / ethyl acetate / 760 Torr

8: tetrahydrofuran

9: 90 percent / OsO₄, N-Methylmorpholine N-oxide, H₂O / acetone; H₂O / stereoselection: 23/1

10: 93 percent / NaH / dimethylformamide

11: 4N HCl / tetrahydrofuran

With lead(IV) acetate; hydrogenchloride; osmium(VIII) oxide; molecular sieve; sulfuric acid; water; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4039(00)88188-5

Reference yield:

: 53929-15-0,53929-22-9,87641-33-6,87641-34-7,96918-47-7,96997-30-7
1-((3aR,5R,6S,6aR)-6-Methoxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanol

: 98003-91-9
(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / PCC, mol.sieve / CH₂Cl₂

2: 89 percent / K₂CO₃ / methanol

3: 100 percent / Hydrogen / Pd/C / ethyl acetate / 760 Torr

4: tetrahydrofuran

5: 90 percent / OsO₄, N-Methylmorpholine N-oxide, H₂O / acetone; H₂O / stereoselection: 23/1

6: 93 percent / NaH / dimethylformamide

7: 4N HCl / tetrahydrofuran

With hydrogenchloride; osmium(VIII) oxide; molecular sieve; water; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)88188-5

Reference yield:

: 53929-10-5,53929-19-4,96918-49-9,96918-53-5
1-((3aR,5R,6S,6aR)-6-Methoxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

: 98003-91-9
(2S,3R,4S,5R)-5-[(1S,2R)-1-Hydroxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-4-methyl-tetrahydro-furan-2,3-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 61 percent / Pb(OAc)4 / benzene

2: 90 percent / diethyl ether / diastereomers ratio 4:1

3: 91 percent / PCC, mol.sieve / CH₂Cl₂

4: 89 percent / K₂CO₃ / methanol

5: 100 percent / Hydrogen / Pd/C / ethyl acetate / 760 Torr

6: tetrahydrofuran

7: 90 percent / OsO₄, N-Methylmorpholine N-oxide, H₂O / acetone; H₂O / stereoselection: 23/1

8: 93 percent / NaH / dimethylformamide

9: 4N HCl / tetrahydrofuran

With lead(IV) acetate; hydrogenchloride; osmium(VIII) oxide; molecular sieve; water; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4039(00)88188-5