(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

Base Information

Chemical Name:(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane
CAS No.:139435-01-1
Molecular Formula:C₃₀H₃₇NO₄SSi
Molecular Weight:535.78
Hs Code.:

Synonyms:(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

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Chemical Property of (1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

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Technology Process of (1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

There total 8 articles about (1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane 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:

: 146324-57-4
N-[(1S,2R,3S,4S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-(tetrahydro-pyran-2-yloxymethyl)-bicyclo[2.2.1]hept-2-yl]-benzenesulfonamide

: 139435-01-1
(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 50 ℃; Yield given;
DOI:10.1248/cpb.39.2842

Reference yield:

: 287395-35-1
(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 139435-01-1
(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: p-toluenesulfonic acid hydrate / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) 6 N NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 1.5 h, 2.) 60 deg C, 1 h

5: 2.15 g / dimethylaminopyridine / dimethylformamide / 50 °C

6: AcOH / tetrahydrofuran; H₂O / 50 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.2842

Reference yield:

: 76197-78-9,151292-69-2
(1S,2S,3S,4R)-3-Isocyanato-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 139435-01-1
(1S,2S,3R,4S,5R)-5-tert-butyldiphenylsilyloxy-2-hydroxymethyl-3-phenylsulfonylaminobicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / benzene / 1 h / Heating

2: CF₃CO₂H / various solvent(s) / 6 h / 45 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

5: p-toluenesulfonic acid hydrate / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) 6 N NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 1.5 h, 2.) 60 deg C, 1 h

7: 2.15 g / dimethylaminopyridine / dimethylformamide / 50 °C

8: AcOH / tetrahydrofuran; H₂O / 50 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2842