(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Base Information

Chemical Name:(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
CAS No.:189558-00-7
Molecular Formula:C₃₆H₃₈O₈Si
Molecular Weight:626.778
Hs Code.:

(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Chemical Property of (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Technology Process of (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

There total 9 articles about (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol 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:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 189558-00-7
(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 30 h / Ambient temperature

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

3: 68 percent / tetrahydrofuran; toluene / 4 h / Ambient temperature

4: 1.) OsO₄, NMO, 2.) 5percent NaHSO₃ / 1.) H₂O, acetone, 5 deg C, overnight, 2.) H₂O

5: 83 percent / DCC, TFA, Py / benzene; dimethylsulfoxide / 20 h / Ambient temperature

6: tetrahydrofuran / 6 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; sodium hydrogensulfite; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1271/bbb.61.743

Reference yield:

: 189557-84-4
(3R,4S,5S)-5-Benzo[1,3]dioxol-5-yl-4-hydroxymethyl-tetrahydro-furan-3-ol

: 189558-00-7
(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 30 h / Ambient temperature

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

3: 68 percent / tetrahydrofuran; toluene / 4 h / Ambient temperature

4: 1.) OsO₄, NMO, 2.) 5percent NaHSO₃ / 1.) H₂O, acetone, 5 deg C, overnight, 2.) H₂O

5: 83 percent / DCC, TFA, Py / benzene; dimethylsulfoxide / 20 h / Ambient temperature

6: tetrahydrofuran / 6 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; sodium hydrogensulfite; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1271/bbb.61.743

Reference yield:

: (R)-3-[Benzo[1,3]dioxol-5-yl-(tetrahydro-pyran-2-yloxy)-methyl]-4-hydroxy-dihydro-furan-2-one

: 189558-00-7
(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) LiAlH₄, 2.) TsOH / 1.) THF, -10 deg C, 1 h, 2.) MeOH 50 deg C, 12 h.

2: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 30 h / Ambient temperature

3: 1.) oxalyl chloride, DMSO, 1.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 30 min.

4: 68 percent / tetrahydrofuran; toluene / 4 h / Ambient temperature

5: 1.) OsO₄, NMO, 2.) 5percent NaHSO₃ / 1.) H₂O, acetone, 5 deg C, overnight, 2.) H₂O

6: 83 percent / DCC, TFA, Py / benzene; dimethylsulfoxide / 20 h / Ambient temperature

7: tetrahydrofuran / 6 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; toluene-4-sulfonic acid; sodium hydrogensulfite; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1271/bbb.61.743