63593-03-3

Basic information

• Product Name: 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE
• Synonyms: ((3aR,6S,6aR);-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl);3-O-benzyl-4-C-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose;3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE;3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose;3-O-Benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose;3-O-Benzyl-4-(hydroxyMethyl)-1,2-O-isopropylidene-alfa-D-ribofuranose;a-D-erythro-Pentofuranose,4-C-(hydroxyMethyl)-1,2-O -(1-Methylethylidene)-3-O-(phenylMethyl)-
• CAS NO: 63593-03-3
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.34200
• EINECS: 1806241-263-5
• Mol File: 63593-03-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 442.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.29
• Storage Temp.: 2-8°C
• PKA: 13.95±0.10(Predicted)
• CAS DataBase Reference: 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE(63593-03-3)
• EPA Substance Registry System: 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE(63593-03-3)

Safety Data

• Hazardous Substances Data: 63593-03-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

formaldehyd (50-00-0) + 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane Cannizzaro reaction;	94%
With sodium hydroxide In 1,4-dioxane at 28 - 30℃; for 16.83h;	75%
With sodium hydroxide In tetrahydrofuran; water at 20℃;	47%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;	47%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃;	52.5 g

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose (620630-82-2) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaIO4 / methanol 2: 94 percent / aq. NaOH / dioxane View Scheme
Multi-step reaction with 2 steps 1: sodium periodate / water / 1 h / 0 °C 2: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 2: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose (22331-21-1) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. HCl / ethanol 2: aq. NaIO4 / methanol 3: 94 percent / aq. NaOH / dioxane View Scheme
Multi-step reaction with 3 steps 1: acetic acid / water / 72 h / 20 °C 2: sodium periodate / water / 1 h / 0 °C 3: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / water / 20 - 25 °C / Large scale 2: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 3: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

formaldehyd (50-00-0) + 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 144h;	77 g

Diacetone D-glucose (2595-05-3) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere 1.2: 4.5 h / 0 °C 2.1: acetic acid / water / 72 h / 20 °C 3.1: sodium periodate / water / 1 h / 0 °C 4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 2: acetic acid / water / 20 - 25 °C / Large scale 3: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 4: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

benzyl bromide (100-39-0) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere 1.2: 4.5 h / 0 °C 2.1: acetic acid / water / 72 h / 20 °C 3.1: sodium periodate / water / 1 h / 0 °C 4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid; water / 20 °C 3.1: sodium periodate / water; methanol / 1 h / 20 °C 4.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid / water / 20 °C 3.1: sodium periodate / water; methanol / 1 h / 20 °C 4.1: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid / water / 20 °C 3.1: sodium periodate / methanol; water / 1 h / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme

3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (1013943-40-2) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; water / 20 °C 2: sodium periodate / water; methanol / 1 h / 20 °C 3: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / water / 20 °C 2: sodium periodate / water; methanol / 1 h / 20 °C 3: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / water / 20 °C 2: sodium periodate / methanol; water / 1 h / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme

C16H22O6 → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium periodate / water; methanol / 1 h / 20 °C 2: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium periodate / water; methanol / 1 h / 20 °C 2: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium periodate / methanol; water / 1 h / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme

D-glucofuranose (610-85-5, 7045-51-4, 19217-07-3, 30412-16-9, 34685-37-5, 36468-79-8, 36468-80-1, 36468-81-2, 36468-82-3, 36468-84-5, 36574-15-9, 36574-18-2, 36574-19-3, 36574-21-7, 36972-23-3, 36978-43-5, 37738-80-0, 40461-75-4, 40461-79-8, 40461-80-1, 40461-83-4, 40550-49-0, 41612-82-2, 41846-85-9, 41846-86-0, 41846-87-1, 41846-88-2, 41846-89-3, 41846-90-6, 41846-91-7, 41846-92-8, 41846-93-9, 41846-94-0, 41846-95-1, 41846-96-2, 41846-97-3, 41847-47-6, 41847-48-7, 41847-49-8, 41847-50-1, 41847-62-5, 41847-63-6, 41847-64-7, 41847-65-8, 41847-66-9, 41847-67-0, 41847-68-1, 51076-04-1, 89673-68-7, 131064-93-2, 131064-94-3, 131064-95-4, 131064-96-5, 131064-97-6, 131065-02-6, 131065-03-7, 131065-04-8, 131065-05-9, 131065-06-0) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: zinc(II) chloride; phosphoric acid / 15 - 30 °C / Large scale 2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C 3: sodium tetrahydroborate / water / 10 - 15 °C 4: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 5: acetic acid / water / 20 - 25 °C / Large scale 6: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 7: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C 2: sodium tetrahydroborate / water / 10 - 15 °C 3: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 4: acetic acid / water / 20 - 25 °C / Large scale 5: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 6: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / water / 10 - 15 °C 2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 3: acetic acid / water / 20 - 25 °C / Large scale 4: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 5: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme

vinyl acetate (108-05-4) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 5-O-acetyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions	Yield
With candida antarctica lipase-B In di-isopropyl ether at 45℃; for 1.5h; Reagent/catalyst; Solvent; Green chemistry; Enzymatic reaction; regioselective reaction;	100%

acetic anhydride (108-24-7) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 4-C-(acetoxymethyl)-5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions	Yield
With dmap In dichloromethane; water at 20℃;	99%

methanesulfonyl chloride (124-63-0) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (293751-01-6)

Conditions	Yield
With pyridine at 20℃; for 1h;	98%
With pyridine at 0 - 20℃; for 1h;	98%
With pyridine In dichloromethane	98%

propionic acid anhydride (123-62-6) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3-O-benzyl-1,2-O-isopropylidene-5-O-propanoyl-4-C-[(propanoyloxy)methyl]-α-D-ribofuranose

Conditions	Yield
With dmap In dichloromethane; water at 20℃;	98%

butanoic acid anhydride (106-31-0) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3-O-benzyl-5-O-butanoyl-4-C-[(butanoyloxy)methyl]-1,2-O-isopropylidene-α-D-ribofuranose

Conditions	Yield
With dmap In dichloromethane; water at 20℃;	98%

acetic anhydride (108-24-7) + thymin (65-71-4) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-(2,5-di-O-acetyl-4-C-acetyloxymethyl-3-O-benzyl-β-D-erythro-pentofuranosyl)thymine (552856-36-7)

Conditions	Yield
Stage #1: acetic anhydride; 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sulfuric acid In water; acetic acid at 0 - 20℃; for 2.41667h; Stage #2: thymin With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 80℃; for 5h; Heating / reflux;	91%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8)

Conditions	Yield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	73%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5 - 20℃; for 3h;	69%
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	69%

tert-butylchlorodiphenylsilane (58479-61-1) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol (212970-72-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 14h; Etherification; Silylation;	67%
In dichloromethane at 20℃; for 11h;	67%

benzyl chloride (100-44-7) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose + {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol (153186-11-9) + ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at -9℃; for 1h;	A 10% B 11% C 66%

tert-butylchlorodiphenylsilane (58479-61-1) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol (212970-72-4) + {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane for 1h; Heating;	A 38% B 62%

tert-butyldimethylsilyl chloride (18162-48-6) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → C22H36O6Si (945628-28-4) + C22H36O6Si (314256-39-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;	A 22% B 59%

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8)

Conditions	Yield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: With benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;	51%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose + {(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol (153186-11-9) + ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8)

Conditions	Yield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With di(n-butyl)tin oxide In methanol for 1h; Substitution; Heating; Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene for 15h; Etherification; Heating;	A 23% B 21% C 19%

acetic anhydride (108-24-7) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → Acetic acid (3S,4R)-4,5-diacetoxy-2-acetoxymethyl-3-benzyloxy-tetrahydro-furan-2-ylmethyl ester (552856-35-6)

Conditions	Yield
With sulfuric acid In acetic acid at 20℃; for 2h;	258 mg
With sulfuric acid In acetic acid at 0 - 20℃; for 2.41667h;

benzoyl chloride (98-88-4) + 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (552856-52-7)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-thymine (945382-96-7)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: acetic acid; triflic acid / 0.5 h 8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → C27H30N2O6

Conditions

Yield

Multi-step reaction with 9 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: acetic acid; triflic acid / 0.5 h 8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C 9.1: ammonia / methanol View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine (945382-98-9)

Conditions

Yield

Multi-step reaction with 10 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: acetic acid; triflic acid / 0.5 h 8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C 9.1: ammonia / methanol 10.1: 4.1 g / DMAP; pyridine View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,3R,4R,5R,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

Conditions

Yield

Multi-step reaction with 11 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: acetic acid; triflic acid / 0.5 h 8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C 9.1: ammonia / methanol 10.1: 4.1 g / DMAP; pyridine 11.1: Bu3SnH / toluene / 0.5 h / Heating 11.2: 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,3R,4R,5S,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

Conditions

Yield

Multi-step reaction with 11 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: acetic acid; triflic acid / 0.5 h 8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C 9.1: ammonia / methanol 10.1: 4.1 g / DMAP; pyridine 11.1: Bu3SnH / toluene / 0.5 h / Heating 11.2: 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose (945383-09-5)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → C25H30O6

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3,5-di-O-benzyl-4-C-penten-yl-1,2-O-isopropylidene-α-D-ribofuranose (945383-12-0)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → C27H32O7

Conditions

Yield

Multi-step reaction with 10 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane 10.1: acetic acid; triflic acid / 0.5 h / ice bath View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → C30H34N2O7 (945383-14-2)

Conditions

Yield

Multi-step reaction with 11 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane 10.1: acetic acid; triflic acid / 0.5 h / ice bath 11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 11.2: TMSOTf / acetonitrile / 0 - 20 °C View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine (945383-16-4)

Conditions

Yield

Multi-step reaction with 12 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane 10.1: acetic acid; triflic acid / 0.5 h / ice bath 11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 11.2: TMSOTf / acetonitrile / 0 - 20 °C 12.1: 2.8 g / ammonia / methanol View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine (945383-18-6)

Conditions

Yield

Multi-step reaction with 13 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane 10.1: acetic acid; triflic acid / 0.5 h / ice bath 11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 11.2: TMSOTf / acetonitrile / 0 - 20 °C 12.1: 2.8 g / ammonia / methanol 13.1: 60 percent / DMAP; pyridine View Scheme

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane (945383-20-0)

Conditions

Yield

Multi-step reaction with 14 steps 1.1: 66 percent / NaH / -5 - 20 °C 2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 17 g / tetrahydrofuran; hexane / -78 °C 4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 6.2: 12 g / tetrahydrofuran; hexane / -78 °C 7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran 7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C 8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C 9.1: BuLi / tetrahydrofuran; hexane / -78 °C 9.2: 3.5 g / tetrahydrofuran; hexane 10.1: acetic acid; triflic acid / 0.5 h / ice bath 11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating 11.2: TMSOTf / acetonitrile / 0 - 20 °C 12.1: 2.8 g / ammonia / methanol 13.1: 60 percent / DMAP; pyridine 14.1: Bu3SnH / toluene / 0.25 h / Heating 14.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating View Scheme

Upstream product

• 100-39-0 benzyl bromide 
• 2595-05-3 Diacetone D-glucose 
• 50-00-0 formaldehyd 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 40982-92-1 (3aR,5R,6R,6aR)-6-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 26597-74-0 1,2:5,6-di-O-isopropylidene-β-L-talofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 1013943-40-2 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 945628-28-4 C₂₂H₃₆O₆Si 
• 314256-39-8 C₂₂H₃₆O₆Si 
• 1610605-77-0 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one 
• 293751-16-3 (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 1610605-78-1 N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide 
• 1610605-69-0 N-(9-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide 
• 1610605-72-5 N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide 
• 1160287-68-2 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one 
• 1160287-69-3 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one 
• 1094603-21-0 (2R,3R,4S)-4-(benzyloxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate 
• 405290-35-9 9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine 
• 1610605-73-6 ((1R,3R,4R,7S)-3-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylmethanesulfonate 
• 1610605-66-7 ((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate 
• 1094603-22-1 ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate 

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