3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose

Base Information

Chemical Name:3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose
CAS No.:98003-88-4
Molecular Formula:C₂₁H₃₂O₆
Molecular Weight:380.481
Hs Code.:

Synonyms:3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose

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Chemical Property of 3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose

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Technology Process of 3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose

There total 13 articles about 3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose 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: 93.2%

: 98003-85-1
3,7,8,-trideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-α-D-glycero-D-gulo-octofuranose

: 824-94-2
p-methoxybenzyl chloride

: 98003-88-4
3,7,8-trideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-D-glycero-D-gulo-hexafuranose

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature; 1.) 30 min, RT; 2.) 2 h, rt; 3.) 50 deg C, 1 h;

Reference yield: 93.0%

: 87641-39-2,98003-85-1,98003-86-2
(2S,3R)-2-((3aR,5R,6R,6aR)-2,2,6-Trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pentane-2,3-diol

: 824-94-2
p-methoxybenzyl chloride

: 87641-43-8,98003-88-4
(2S,3R)-3-(4-Methoxy-benzyloxy)-2-((3aR,5R,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pentan-2-ol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)88188-5

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

: 87641-43-8,98003-88-4
(2S,3R)-3-(4-Methoxy-benzyloxy)-2-((3aR,5R,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pentan-2-ol

Guidance literature:: Multi-step reaction with 10 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

With lead(IV) acetate; 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