3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

Base Information

Chemical Name:3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde
CAS No.:194039-11-7
Molecular Formula:C₃₀H₄₂O₇Si
Molecular Weight:542.745
Hs Code.:

Synonyms:3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

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Chemical Property of 3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

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Technology Process of 3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

There total 9 articles about 3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde 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: 90.0%

: 203925-43-3
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

: 194039-11-7
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine;
DOI:10.1021/ja973287h

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 194039-11-7
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: (+/-)-camphorsulfonic acid, 4 Angstroem molecular sieves / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 93 percent / Et₃N

3: 87 percent / 9-BBN, H₂O₂

4: 90 percent / oxalyl chloride, DMSO, Et₃N

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja973287h

Reference yield:

: 194039-07-1
methyl 3-O-benzyl-α-D-altropyranoside

: 194039-11-7
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: acetonitrile / 2.5 h / 70 - 80 °C

2: TMSOTf / acetonitrile / 12 h / Ambient temperature

3: (+/-)-camphorsulfonic acid, 4 Angstroem molecular sieves / CH₂Cl₂ / 3.5 h / Ambient temperature

4: 93 percent / Et₃N

5: 87 percent / 9-BBN, H₂O₂

6: 90 percent / oxalyl chloride, DMSO, Et₃N

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In dichloromethane; acetonitrile;
DOI:10.1021/ja973287h