(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

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Chemical Name:(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran
CAS No.:256413-35-1
Molecular Formula:C₃₀H₅₆O₆Si₂
Molecular Weight:568.942
Hs Code.:

Synonyms:(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

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Chemical Property of (2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

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Technology Process of (2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

There total 12 articles about (2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: (3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-ol

: 256413-35-1
(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

: (2R,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 6h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9 DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

: 71676-30-7,87508-17-6,138922-03-9,87508-18-7
phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

: 256413-35-1
(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 87 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

3.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

4.1: 97 percent / pyridine / 12 h / 0 - 25 °C

5.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

6.1: NaH / dimethylformamide / 0.08 h / 0 °C

6.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NBS; H₂O / acetone / 2 h / 0 - 25 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; water; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ethanethiol; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Reduction / 6.1: Metallation / 6.2: Methylation / 7.1: Hydrolysis / 8.1: Etherification;
DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

: 179072-68-5
phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside

: 256413-35-1
(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

2.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

3.1: 97 percent / pyridine / 12 h / 0 - 25 °C

4.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

6.1: 95 percent / NBS; H₂O / acetone / 2 h / 0 - 25 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; water; zinc trifluoromethanesulfonate; sodium hydride; ethanethiol; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Tosylation / 4.1: Reduction / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrolysis / 7.1: Etherification;
DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L