[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:512782-05-7
Molecular Formula:C₂₂H₃₇IO₅Si
Molecular Weight:536.523
Hs Code.:

Synonyms:[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

There total 12 articles about [(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol 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: 98.0%

: 512782-04-6
Acetic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-ylmethyl ester

: 512782-05-7
[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With sodium methylate; In methanol;
DOI:10.3987/com-01-s(m)6

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 512782-05-7
[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / TfOH / diethyl ether / 0.33 h / 20 °C

2: 64 percent / toluene / 0.33 h / -50 - -20 °C

3: 98 percent / 9-BBN; H₂O₂; OH^(1-) / tetrahydrofuran / 12 h / 20 °C

4: 95 percent / tetrahydrofuran; aq. HCl / 1 h / 20 °C

5: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6: 95 percent / aq. HF / acetonitrile / -20 °C

7: 94 percent / Ph₃P; I₂; imidazole / toluene; acetonitrile / Heating

8: 98 percent / NaOMe / methanol

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; hydrogen fluoride; hydroxide; dihydrogen peroxide; iodine; sodium methylate; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 2: Tebbe olefination;
DOI:10.3987/com-01-s(m)6

Reference yield:

: 143289-36-5
2,3:4,6-Di-O-isopropylidene-D-mannopyranonolactone

: 512782-05-7
[(2R,3S,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 11 steps

1: 79 percent / NaH / tetrahydrofuran / -78 - -40 °C

2: 99 percent / SmI₂; HOCH₂CH₂OH; HMPA / tetrahydrofuran / 0.5 h / 20 °C

3: 87 percent / TfOH / diethyl ether / 0.33 h / 20 °C

4: 64 percent / toluene / 0.33 h / -50 - -20 °C

5: 98 percent / 9-BBN; H₂O₂; OH^(1-) / tetrahydrofuran / 12 h / 20 °C

6: 95 percent / tetrahydrofuran; aq. HCl / 1 h / 20 °C

7: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

8: 95 percent / aq. HF / acetonitrile / -20 °C

9: 94 percent / Ph₃P; I₂; imidazole / toluene; acetonitrile / Heating

10: 98 percent / NaOMe / methanol

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; trifluorormethanesulfonic acid; hydrogen fluoride; hydroxide; dihydrogen peroxide; iodine; sodium methylate; sodium hydride; ethylene glycol; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 4: Tebbe olefination;
DOI:10.3987/com-01-s(m)6