HCID 70360554, compound → [(2R,3R,4R,5S)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol

HRID 1073445Notes

Reaction equation

HRID 1073445 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@H:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:33]([CH2:43][O:44]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[O:32][C@H:10]2[CH2:11][O:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C>[C:1]1([CH2:7][O:8][C@H:9]2[C@H:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:33]([CH2:43][OH:44])[O:32][C@H:10]2[CH2:11][OH:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 70360554HCID 70360554, compound

Product 1

HCID 11210109[(2R,3R,4R,5S)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In accordance with Flowchart C, 2,5-anhydro-D-glucitol 19 is reacted with trityl chloride in pyridine, giving 2,5-anhydro-1,6-bis-O-(triphenylmethyl)-D-glucitol 20, which is then reacted with sodium hydride and benzyl bromide in dimethylformamide, giving 2,5-anhydro-3,4-bis-O-(phenylmethyl)-1,6-bis-O-(triphenylmethyl)-D-glucitol 21. Compound 21 is then reacted with acetic acid at about 80° C., giving 2,5-anhydro-3,4-bis-O-(phenylmethyl)-D-glucitol 22, which is then reacted with diphenyl phosphorochloridate in pyridine at reduced temperature, giving 2,5-anhydro-3,4-bis-O-(phenylmethyl)-D-glucitol, 1,6-bis(diphenyl phosphate) 23. Substitution of other esterifying agents as described in Flowchart A will result in the corresponding tetraesters. Compound 23 is then hydrogenated in methanol/acetic acid over palladium on carbon, giving the product of Formula I where R', R", R'" and R"are phenyl, 2,5-anhydro-D-glucitol, 1,6-bis(diphenyl phosphate) 24. which may then be hydrogenated in methanol over platinum oxide, giving the product of Formula I where R', R", R'" and R"" are hydrogen, 2,5-anhydro-D-glucitol, 1,6-bis(dihydrogen phosphate) 25. Compounds 24 and 25 are disclosed in Voll et al., Carbohydrate Research, 95, 145-154 (1981), but are prepared by a different process. ##STR16##

Sources & evidence

ORD record
ord-738375567e284661a78e48bf1fc6c25b
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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