(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

Base Information

Chemical Name:(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one
CAS No.:148903-90-6
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

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Chemical Property of (Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

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Technology Process of (Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

There total 8 articles about (Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one 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: 84.0%

: 148903-89-3
(Z)-(8S,9R)-8-tert-butyldiphenylsilyloxy-9-tert-butyldiphenylsilyloxymethyl-2,3,4,7,8,9-hexahydro-oxonin-2-one

: 148903-90-6
(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

Guidance literature:: With pyridine; hydrogen fluoride; In tetrahydrofuran;
DOI:10.1021/ja00066a056

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 148903-90-6
(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: HCl / diethyl ether / 0.25 h

2: pyridine / 0.5 h / Ambient temperature

3: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

4: 72 percent / tetrahydrofuran / 2 h / -70 - 0 °C

5: 98 percent / PPTS / toluene / 1.5 h / Heating

6: NaIO₄, NaHCO₃ / methanol; CH₂Cl₂; diethyl ether; H₂O / 2 h / Ambient temperature

7: DBU / toluene / 16 h / Heating

8: 84 percent / HF, pyridine / tetrahydrofuran

With pyridine; hydrogenchloride; sodium periodate; boron trichloride - methyl sulfide complex; hydrogen fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/ja00066a056

Reference yield:

: 3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-D-ribofuranose

: 148903-90-6
(Z)-(8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-hydroxymethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / tetrahydrofuran / 2 h / -70 - 0 °C

2: 98 percent / PPTS / toluene / 1.5 h / Heating

3: NaIO₄, NaHCO₃ / methanol; CH₂Cl₂; diethyl ether; H₂O / 2 h / Ambient temperature

4: DBU / toluene / 16 h / Heating

5: 84 percent / HF, pyridine / tetrahydrofuran

With pyridine; sodium periodate; hydrogen fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/ja00066a056