(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

Chemical Name:(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:157794-12-2
Molecular Formula:C₃₂H₃₆O₆
Molecular Weight:516.634
Hs Code.:

Synonyms:(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

There total 15 articles about (2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-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: 75.0%

: (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S)-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

: (S)-1-((2R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-prop-2-en-1-ol

: 157794-12-2
(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; -20 deg C to room t.;
DOI:10.1016/S0040-4039(00)73310-7

Reference yield:

: 58341-62-1
methyl 2-O-allyl-3-O-benzyl-α-D-glucopyranoside

: 157794-12-2
(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaH / 2.) THF, DMF, 0 deg C to room t.

2: TMSOTf / acetonitrile / Ambient temperature

3: 65 percent / (Ph₃P)4RhH, TFA / ethanol / 0.75 h / Heating

4: 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, room t.

6: benzene / 50 °C

7: 90 percent / DIBAL / CH₂Cl₂ / -78 °C

8: 92 percent / t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem mol. sieves / CH₂Cl₂ / -25 °C

9: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 °C

10: 1.) KHMDS / 2.) THF, 0 deg C to room t.

11: 98 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

12: 5 percent / camphorsulfonic acid / CH₂Cl₂ / -20 deg C to room t.

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; hydridotetakis(triphenylphosphine)rhodium(I); pyridine-SO₃ complex; dimethylsulfide; diethyl (2R,3R)-tartrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)73310-7

Reference yield:

: 58341-63-2
methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside

: 157794-12-2
(2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1: TMSOTf / acetonitrile / Ambient temperature

2: 65 percent / (Ph₃P)4RhH, TFA / ethanol / 0.75 h / Heating

3: 2,6-lutidine / CH₂Cl₂ / 0 °C

4: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, room t.

5: benzene / 50 °C

6: 90 percent / DIBAL / CH₂Cl₂ / -78 °C

7: 92 percent / t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem mol. sieves / CH₂Cl₂ / -25 °C

8: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 °C

9: 1.) KHMDS / 2.) THF, 0 deg C to room t.

10: 98 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

11: 5 percent / camphorsulfonic acid / CH₂Cl₂ / -20 deg C to room t.

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; hydridotetakis(triphenylphosphine)rhodium(I); pyridine-SO₃ complex; dimethylsulfide; diethyl (2R,3R)-tartrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)73310-7