(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Base Information

Chemical Name:(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran
CAS No.:163563-92-6
Molecular Formula:C₂₉H₃₂O₅
Molecular Weight:460.57
Hs Code.:

Synonyms:(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Suppliers and Price of (3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

There total 16 articles about (3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-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: 74.0%

: 942041-40-9
methyl 3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

: 163563-92-6
(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene;
DOI:10.1021/jo00116a008

Reference yield:

: 942041-32-9
C₂₀H₂₆O₆

: 163563-92-6
(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 9 steps

1.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

2.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

3.1: BH₃*Me₃S; NaOH; H₂O₂ / tetrahydrofuran / 24 h

3.2: oxalyl chloride; DMSO / CH₂Cl₂ / 4 h / -78 °C

4.1: 94 percent / Et₃N / CH₂Cl₂ / 168 h / 20 °C

5.1: 92 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.17 h / 0 °C

6.1: 78 percent / NaH / dimethylformamide / 1 h / 20 °C

7.1: 66 percent / Cu(OTf)2; BH₃*THF / 1 h

8.1: 86 percent / PPh₃; I₂; imidazole / toluene / 3 h / Heating

9.1: 60 percent / DBU / tetrahydrofuran / Heating

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; borane-THF; water; dihydrogen peroxide; iodine; copper(II) bis(trifluoromethanesulfonate); sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 163563-92-6
(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 14 steps

1.1: Bu₂SnO / toluene; methanol / 14 h / 55 °C

1.2: Et₃N / dioxane / 4 h / 20 °C

2.1: 95 percent / P-TsOH / CH₂Cl₂ / 1 h / 20 °C

3.1: 96 percent / NaOMe / methanol / 2 h / 20 °C

4.1: TFAA; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: n-BuLi / tetrahydrofuran / -78 °C

6.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

7.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

8.1: BH₃*Me₃S; NaOH; H₂O₂ / tetrahydrofuran / 24 h

8.2: oxalyl chloride; DMSO / CH₂Cl₂ / 4 h / -78 °C

9.1: 94 percent / Et₃N / CH₂Cl₂ / 168 h / 20 °C

10.1: 92 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.17 h / 0 °C

11.1: 78 percent / NaH / dimethylformamide / 1 h / 20 °C

12.1: 66 percent / Cu(OTf)2; BH₃*THF / 1 h

13.1: 86 percent / PPh₃; I₂; imidazole / toluene / 3 h / Heating

14.1: 60 percent / DBU / tetrahydrofuran / Heating

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; borane-THF; water; dihydrogen peroxide; iodine; sodium methylate; copper(II) bis(trifluoromethanesulfonate); sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2007.03.031