(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

Base Information

Chemical Name:(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde
CAS No.:190380-82-6
Molecular Formula:C₃₀H₃₄O₇Si
Molecular Weight:534.681
Hs Code.:

Synonyms:(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

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Chemical Property of (3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

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Technology Process of (3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

There total 6 articles about (3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde 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: 88.0%

: 190380-81-5
(3R,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-ol

: 190380-82-6
(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

Guidance literature:: With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dimethyl sulfoxide; benzene; for 20h; Ambient temperature;
DOI:10.1271/bbb.61.660

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 190380-82-6
(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N, DMAP / CH₂Cl₂; dimethylformamide / 24 h / Heating

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 30 min

3: 73 percent / toluene; tetrahydrofuran / 4 h / -78 - 20 °C

4: 83 percent / OsO₄, NMO / H₂O; acetone / 5 °C

5: 88 percent / DCC, TFA, Py / dimethylsulfoxide; benzene / 20 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1271/bbb.61.660

Reference yield:

: 190380-77-9
(3R,4S,5S)-4-Hydroxymethyl-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-ol

: 190380-82-6
(3S,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(6-methoxy-benzo[1,3]dioxol-5-yl)-tetrahydro-furan-3-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N, DMAP / CH₂Cl₂; dimethylformamide / 24 h / Heating

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 30 min

3: 73 percent / toluene; tetrahydrofuran / 4 h / -78 - 20 °C

4: 83 percent / OsO₄, NMO / H₂O; acetone / 5 °C

5: 88 percent / DCC, TFA, Py / dimethylsulfoxide; benzene / 20 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1271/bbb.61.660