1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

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Chemical Name:1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one
CAS No.:203925-46-6
Molecular Formula:C₄₁H₅₆O₉Si
Molecular Weight:720.976
Hs Code.:

1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

Synonyms:1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

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Chemical Property of 1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

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Technology Process of 1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

There total 15 articles about 1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-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: 89.0%

: 203925-45-5
1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-ol

: 203925-46-6
1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

Guidance literature:: With Dess-Martin periodane;
DOI:10.1021/ja973287h

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 203925-46-6
1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

Guidance literature:: Multi-step reaction with 6 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

5: 1.) t-BuLi / 1.) Et₂O, pentane, -78 deg C, 20 min, 2.) Et₂O, pentane, -78 deg C, 15 min

6: 89 percent / Dess-Martin periodinane

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

Reference yield:

: 74410-51-8
methyl 4,6-O-benzylidene-3-O-benzyl-α-D-altropyranoside

: 203925-46-6
1-[(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]-6-(4-methoxy-benzyloxy)-hexan-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / TsOH / methanol

2: acetonitrile / 2.5 h / 70 - 80 °C

3: TMSOTf / acetonitrile / 12 h / Ambient temperature

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

5: 93 percent / Et₃N

6: 87 percent / 9-BBN, H₂O₂

7: 90 percent / oxalyl chloride, DMSO, Et₃N

8: 1.) t-BuLi / 1.) Et₂O, pentane, -78 deg C, 20 min, 2.) Et₂O, pentane, -78 deg C, 15 min

9: 89 percent / Dess-Martin periodinane

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; dihydrogen peroxide; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja973287h